GB1339101A - Production of phenylalanine derivatives - Google Patents
Production of phenylalanine derivativesInfo
- Publication number
- GB1339101A GB1339101A GB375972A GB1339101DA GB1339101A GB 1339101 A GB1339101 A GB 1339101A GB 375972 A GB375972 A GB 375972A GB 1339101D A GB1339101D A GB 1339101DA GB 1339101 A GB1339101 A GB 1339101A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylalanine
- aspartyl
- alkyl esters
- protected
- tertiary
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002993 phenylalanine derivatives Chemical class 0.000 title 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229960005190 phenylalanine Drugs 0.000 abstract 2
- CBCWFFVMFVTTKU-LURJTMIESA-N (2s)-2-(2-methylbutan-2-yloxycarbonylamino)butanedioic acid Chemical compound CCC(C)(C)OC(=O)N[C@H](C(O)=O)CC(O)=O CBCWFFVMFVTTKU-LURJTMIESA-N 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- KAJBMCZQVSQJDE-YFKPBYRVSA-N Nalpha-(tert-butoxycarbonyl)-l-aspartic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC(O)=O KAJBMCZQVSQJDE-YFKPBYRVSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Peptides Or Proteins (AREA)
Abstract
1339101 α-L-Aspartyl-L-phenylalanine alkyl esters G D SEARLE & CO 26 Jan 1972 3759/72 Heading C2C α-L-Aspartyl-L-phenylalanine C 1-4 alkyl esters of the formula in which R is C 1-4 alkyl are obtained by reacting N-protected-L-aspartic anhydrides, in which the N atoms are protected by tertiary-butoxy carbonyl or tertiary-amyloxycarbonyl groups, with C 1-4 alkyl esters of phenylalanine in inert organic solvents to form mixtures of N-protected- α-L-aspartyl-L-phenylalanine C 1-4 alkyl esters and N-protected-#-L-aspartyl-L-phenylalanine C 1-4 alkyl esters: and thereafter either (a) separating all or substantially all of the N-protected-#-L-aspartyl-L-phenylalanine C 1-4 alkyl esters from the N-protected-α-L-aspartyl-L- phenylalanine C 1-4 alkyl esters and eliminating the N-protecting groups from the N-protected-α- L-aspartyl-L-phenylalanine C 1-4 alkyl esters, or (b) eliminating the N-protecting groups from the mixtures of N-protected-α- and #-aspartyl-L- phenylalanine C 1-4 alkyl esters and separating all or substantially all of the #-L-aspartyl-L- phenylalanine C 1-4 alkyl esters from the α-L- aspartyl-L-phenylalanine C 1-4 alkyl esters. N-Tertiary-butoxycarbonyl-L-aspartic anhydride and N-tertiary-amyloxycarbonyl-L-aspartic anhydride are obtained by reacting N-tertiarybutoxy-carbonylaspartic acid and N-tertiaryamyloxy-carbonylaspartic acid respectively with acetic anhydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB375972 | 1972-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1339101A true GB1339101A (en) | 1973-11-28 |
Family
ID=9764429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB375972A Expired GB1339101A (en) | 1972-01-26 | 1972-01-26 | Production of phenylalanine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1339101A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2153365A (en) * | 1984-01-26 | 1985-08-21 | Pierrel Spa | Process for the preparation of N-acyl-derivatives of aspartame |
| EP0214550A3 (en) * | 1985-09-09 | 1988-08-10 | Hoechst Aktiengesellschaft | Process for the preparation of aspartame and agent for its preparation |
-
1972
- 1972-01-26 GB GB375972A patent/GB1339101A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2153365A (en) * | 1984-01-26 | 1985-08-21 | Pierrel Spa | Process for the preparation of N-acyl-derivatives of aspartame |
| EP0214550A3 (en) * | 1985-09-09 | 1988-08-10 | Hoechst Aktiengesellschaft | Process for the preparation of aspartame and agent for its preparation |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |