GB739127A - Process for producing threo-1-p-nitrophenyl-2-acylamidopropane-1, 3-diols - Google Patents
Process for producing threo-1-p-nitrophenyl-2-acylamidopropane-1, 3-diolsInfo
- Publication number
- GB739127A GB739127A GB24818/53A GB2481853A GB739127A GB 739127 A GB739127 A GB 739127A GB 24818/53 A GB24818/53 A GB 24818/53A GB 2481853 A GB2481853 A GB 2481853A GB 739127 A GB739127 A GB 739127A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitrophenyl
- aluminium
- threo
- diols
- diol
- 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
- 229910052782 aluminium Inorganic materials 0.000 abstract 4
- 239000004411 aluminium Substances 0.000 abstract 4
- -1 aluminium alkoxide Chemical class 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Substances Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000717 retained effect Effects 0.000 abstract 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Threo - 1 - p - nitrophenyl - 2 - acylaminopropane-1 : 3-diols are made by reducing the corresponding p-nitro-a -acylamino-b -hydroxypropiophenones with an oxidizable aluminium alkoxide in an anhydrous organic solvent in the presence of an aluminium halide. Preferably 0.05-0.2 mol. of aluminium chloride or bromide is used per mole of ketone to be reduced. The products contain little or no erythro isomers and any optical activity is retained during the reduction. Examples show the production of DL-threo-1-p-nitrophenyl-2-acetamidopropane-1 : 3-diol and DL-threo-1-p - nitrophenyl - 2 - dichloracetamidopropane-1 : 3-diol using aluminium isopropylate in isopropanol. Details are given of the reduction with and without the aluminium halide. The acyl group may be derived from a lower aliphatic carboxylic acid or halogen or alkoxy derivative thereof or from benzoic acid or its alkyl, alkoxy, halogen or nitro derivatives. Reference has been directed by the Comptroller to Specification 688,109.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US739127XA | 1953-01-26 | 1953-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB739127A true GB739127A (en) | 1955-10-26 |
Family
ID=22116535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24818/53A Expired GB739127A (en) | 1953-01-26 | 1953-09-08 | Process for producing threo-1-p-nitrophenyl-2-acylamidopropane-1, 3-diols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB739127A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0934923A4 (en) * | 1996-09-13 | 2000-10-04 | Nippon Kayaku Kk | OPTICALLY ACTIVE ERYTHRO-3-AMIDO-2-HYDROXYBUTYRIC ESTERS, AND PROCESS FOR PREPARING THESE ESTERS |
| CN113514582A (en) * | 2021-07-09 | 2021-10-19 | 四川武胜春瑞医药化工有限公司 | Impurity detection method of p-nitro-α-acetamido-β-hydroxypropiophenone |
-
1953
- 1953-09-08 GB GB24818/53A patent/GB739127A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0934923A4 (en) * | 1996-09-13 | 2000-10-04 | Nippon Kayaku Kk | OPTICALLY ACTIVE ERYTHRO-3-AMIDO-2-HYDROXYBUTYRIC ESTERS, AND PROCESS FOR PREPARING THESE ESTERS |
| CN113514582A (en) * | 2021-07-09 | 2021-10-19 | 四川武胜春瑞医药化工有限公司 | Impurity detection method of p-nitro-α-acetamido-β-hydroxypropiophenone |
| CN113514582B (en) * | 2021-07-09 | 2022-07-12 | 四川武胜春瑞医药化工有限公司 | Impurity detection method for p-nitro-alpha-acetamido-beta-hydroxy propiophenone |
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