Trifluoroacetic acid → (2S,4R)-4-hydroxy-2-(5-methyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1527916ノート

反応式

HRID 1527916 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16]C(C)(C)C)[CH2:13][C@H:12]1[C:21]1[O:22][C:23]([CH3:26])=[CH:24][N:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:21]1[O:22][C:23]([CH3:26])=[CH:24][N:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 89768313(2S,4R)-4-tert-butoxy-2-(5-methyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

生成物 1

HCID 89768259(2S,4R)-4-hydroxy-2-(5-methyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester収率 65.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of (2S,4R)-4-tert-butoxy-2-(5-methyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester (2 g, 5.59 mmol) in dichloromethane (15 mL) was added trifluoroacetic acid (1.57 mL) in dichloromethane (1:5) at 0° C. and the mixture was then stirred at room temp. for 16 h. The reaction mixture was neutralized with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude was then purified by column chromatography to give (2S,4R)-4-hydroxy-2-(5-methyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester (1.1 g, 65.1% yield) as an off white solid. MS calcd. for C16H19N2O4 [(M+H)+] 303.0, obsd. 303.4.

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was then purified by column chromatography

出典と根拠

ORDレコード
ord-b2a56a6567834c128f3755e6a528649d
出典データセット
uspto-grants-2015_07
特許番号
US09090559B2

反応ノート

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