AR003195A1 - Procedimiento para preparar un epoxido - Google Patents
Procedimiento para preparar un epoxidoInfo
- Publication number
- AR003195A1 AR003195A1 ARP960103887A AR10388796A AR003195A1 AR 003195 A1 AR003195 A1 AR 003195A1 AR P960103887 A ARP960103887 A AR P960103887A AR 10388796 A AR10388796 A AR 10388796A AR 003195 A1 AR003195 A1 AR 003195A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- base
- epoxide
- group
- sodium
- Prior art date
Links
- 150000002118 epoxides Chemical class 0.000 title abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- -1 allyl acetonide Chemical compound 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 235000019439 ethyl acetate Nutrition 0.000 abstract 1
- 150000003944 halohydrins Chemical class 0.000 abstract 1
- 150000002496 iodine Chemical class 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- FKBSHNBSEUWDAC-UHFFFAOYSA-L lithium sodium dihydroxide Chemical compound [Li+].[OH-].[OH-].[Na+] FKBSHNBSEUWDAC-UHFFFAOYSA-L 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Un procedimiento para sintetizar el epóxido de fórmula (I), que comprende las etapas de: (a) poner en contacto un equivalente de acetonida de alilo defórmula (II), con alrededor de 1 a 2 equivalentes de un agente halogenante, en un solventemezcla do con una base débil acuosa, en un rango de temperaturaentre alrededor de -40°C, y alrededor de 100°C, para formar la halohidrina de la fórmula (III), donde dicho agente halogenante se selecciona del grupo queconsiste de yodo,N-yodosuccinimida, N -bromosuccinimida, N-clorosuccinimida ó 1,3-dicloro-5,5-dimetilhidantoina, pudiéndose combinar las últimas tres con unasal de yodo, donde dicho solvente se selecciona entre el grupo que consiste de diclorometano, IPAC,THF, EtOAc, DMC y NTBE, d onde dicha base débil seselecciona entre alúmina básica o bicarbonato de sodio, y (b) agregar base en agua para obtener la formación de epóxido de fórmula (I), donde dicha base seselecciona del grupo que consiste enhidróxido de litio, hidróxido de sodio, hidróxido de potasio, hidróxido de tetraalquilamonio; cualquier alcóxido delitio, sodio o potasio C1-4; y DIEA.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/512,602 US5728840A (en) | 1994-03-04 | 1995-08-08 | Process for making an epoxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR003195A1 true AR003195A1 (es) | 1998-07-08 |
Family
ID=24039792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP960103887A AR003195A1 (es) | 1995-08-08 | 1996-08-05 | Procedimiento para preparar un epoxido |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5728840A (es) |
| AR (1) | AR003195A1 (es) |
| AU (1) | AU6765296A (es) |
| BR (1) | BR9609879A (es) |
| HR (1) | HRP960369B1 (es) |
| RS (1) | RS49879B (es) |
| TW (1) | TW327635B (es) |
| WO (1) | WO1997006164A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5981759A (en) * | 1997-06-20 | 1999-11-09 | Merck & Co., Inc. | Process for indinavir intermediate |
| GB2341385A (en) | 1998-09-14 | 2000-03-15 | Merck & Co Inc | Recovery of iodide from chemical process waste water |
| US6482952B2 (en) | 2000-06-20 | 2002-11-19 | Merck & Co., Inc. | Process for preparing acetonides |
| US6835860B2 (en) * | 2002-02-01 | 2004-12-28 | Merck & Co., Inc. | Iodohydroxylation of olefins |
| US7601847B2 (en) | 2004-10-26 | 2009-10-13 | Wyeth | Preparation and purification of 4-(indazol-3-yl)phenols |
| US9948496B1 (en) | 2014-07-30 | 2018-04-17 | Silver Peak Systems, Inc. | Determining a transit appliance for data traffic to a software service |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2052907A1 (en) * | 1990-10-11 | 1992-04-12 | Joseph P. Vacca | Hiv protease inhibitors having symmetrical structure |
| CA2057369A1 (en) * | 1990-12-17 | 1992-06-18 | Ann E. Decamp | Stereocontrolled production of hydroxyester, hydroxyamide, and lactone compounds from chiral alpha-amino aldehydes |
| CA2072237A1 (en) * | 1991-07-02 | 1993-01-03 | Merck & Co., Inc. | Stereoselective production of hydroxyamide compounds from chiral -amino epoxides |
| US5169952A (en) * | 1991-07-02 | 1992-12-08 | Merck & Co., Inc. | Stereoselective production of hydroxyamide compounds from chiral α-amino epoxides |
| ES2112880T3 (es) * | 1991-11-08 | 1998-04-16 | Merck & Co Inc | Inhibidores de la proteasa de vih utiles para el tratamiento del sida. |
| GB2270914A (en) * | 1992-09-14 | 1994-03-30 | Merck & Co Inc | HIV protease inhibitor compounds |
| US5463067A (en) * | 1993-07-16 | 1995-10-31 | Merck & Co., Inc. | Process for making HIV protease inhibitors |
| TW380137B (en) * | 1994-03-04 | 2000-01-21 | Merck & Co Inc | Process for making an epoxide |
-
1995
- 1995-08-08 US US08/512,602 patent/US5728840A/en not_active Expired - Lifetime
-
1996
- 1996-07-26 TW TW085109161A patent/TW327635B/zh not_active IP Right Cessation
- 1996-08-05 AR ARP960103887A patent/AR003195A1/es not_active Application Discontinuation
- 1996-08-05 AU AU67652/96A patent/AU6765296A/en not_active Abandoned
- 1996-08-05 WO PCT/US1996/012715 patent/WO1997006164A1/en not_active Ceased
- 1996-08-05 BR BR9609879A patent/BR9609879A/pt not_active Application Discontinuation
- 1996-08-06 HR HR960369A patent/HRP960369B1/xx not_active IP Right Cessation
- 1996-08-07 RS YUP-458/96A patent/RS49879B/sr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5728840A (en) | 1998-03-17 |
| RS49879B (sr) | 2008-08-07 |
| HRP960369A2 (en) | 1998-04-30 |
| HRP960369B1 (en) | 2009-05-31 |
| WO1997006164A1 (en) | 1997-02-20 |
| YU45896A (sh) | 1999-06-15 |
| TW327635B (en) | 1998-03-01 |
| BR9609879A (pt) | 1999-03-23 |
| AU6765296A (en) | 1997-03-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |