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ノート

反応式

HRID 2309078 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b9f9e6e8ac3471b965ffd2db669376f
出典データセット
uspto-grants-1987_09
特許番号
US04692442

反応ノート

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