2-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl ester → 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

HRID 2309078

반응식

HRID 2309078 반응식
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][O:9][C:10](=[O:16])[CH:11]([O:13]CC)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:19]([S:22][C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1[O:28][CH3:29])(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:16])[CH:11]([N:26]2[C@H:23]([S:22][C:19](=[O:21])[CH3:20])[C@@H:24]([O:28][CH3:29])[C:25]2=[O:27])[OH:13])=[CH:17][CH:18]=1)([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 110433162-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl esterHCID 56630779(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

생성물 1

HCID 566076512-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

714 mg of 2-ethoxy-2-hydroxyacetic acid p-nitrobenzyl ester and 4 g of molecular sieve A4 are added to a solution of 245 mg of (3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine in a mixture of 8 ml of toluene and 2 ml of dimethylformamide and the mixture is stirred overnight at room temperature. The molecular sieves are filtered off from the mixture and the filtrate is concentrated by evaporation in vacuo. The residue is chromatographed over silica gel, and by elution with toluene/ethyl acetate (9:1 and 4:1) the title compound, contamined with some glyoxylate, is obtained.

후처리

  1. filtrationThe molecular sieves are filtered off from the mixture
  2. concentrationthe filtrate is concentrated by evaporation in vacuo
  3. customThe residue is chromatographed over silica gel
  4. washby elution with toluene/ethyl acetate (9:1 and 4:1) the title compound
  5. customis obtained

출처 및 근거

ORD 기록
ord-4b9f9e6e8ac3471b965ffd2db669376f
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04692442

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