2-Methoxypropene → (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 732593ノート

反応式

HRID 732593 の反応式
N1C=C[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.COC(C)=C.[C:23]([O:27][C:28]([N:30]1[CH2:34][C@H:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH2:32][C@@H:31]1[C@@H:45]([OH:60])[C@@H:46]([NH:56][C:57](=[O:59])[CH3:58])[CH2:47][C:48]1[CH:53]=[C:52]([F:54])[CH:51]=[C:50]([F:55])[CH:49]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl.CC(C)=O>[C:23]([O:27][C:28]([N:30]1[CH2:34][C@H:33]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[CH2:32][C@@H:31]1[C@H:45]1[O:60][C:3]([CH3:4])([CH3:2])[N:56]([C:57](=[O:59])[CH3:58])[C@H:46]1[CH2:47][C:48]1[CH:49]=[C:50]([F:55])[CH:51]=[C:52]([F:54])[CH:53]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

参加物

6

反応物 3

HCID 83002-MethoxypropeneHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 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 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

実験手順

Add p-toluene sulfonic acid pyridine salt (0.245 g, 1 mmol) and 2-methoxypropene (4.6 mL, 49 mmol) 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). Stir 60 min and concentrate under reduced pressure. Dissolve residue in ethyl acetate and wash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry magnesium sulfate and purify on silica gel with hexanes/ethyl acetate mixtures to give the desired compound as a foam (3.49 g, 61%).

後処理

  1. concentrationconcentrate under reduced pressure
  2. washDissolve residue in ethyl acetate and wash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry magnesium sulfate
  3. custompurify on silica gel with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-07a5b93d69dd48268e17949fca0efc3a
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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