Acetone → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732601ノート

反応式

HRID 732601 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[C@@H:23]([OH:38])[C@@H:24]([NH:34][C:35](=[O:37])[CH3:36])[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:39][C:40]([CH3:42])=O.COC(C)=C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][C@@H:9]1[C@H:23]1[O:38][C:40]([CH3:42])([CH3:39])[N:34]([C:35](=[O:37])[CH3:36])[C@H:24]1[CH2:25][C:26]1[CH:27]=[C:28]([F:33])[CH:29]=[C:30]([F:32])[CH:31]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 180AcetoneHCID 83002-MethoxypropeneHCID 68814707(2R,4R)-2-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 68816295(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester収率 607.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add to a solution of (2R,4R)-2-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.64 g, 10.55 mmol) in dichloromethane (25 mL) and acetone (25 mL) p-toluene sulfonic acid pyridine salt (0.245 g, 1 mmol) and 2-methoxy propene (4.6 mL, 49 mmol). Stir 60 min and concentrate. Dissolve in ethyl acetate and wash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, eluting with hexanes/ethyl acetate mixtures) to give the title compound as a foam (3.49 g, 61%).

後処理

  1. concentrationconcentrate
  2. dissolutionDissolve in ethyl acetate
  3. washwash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. custompurify
  6. wash(silica gel chromatography, eluting with hexanes/ethyl acetate mixtures)

出典と根拠

ORDレコード
ord-5637c2c7aed64c0eaf3b5a657d5f73cc
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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