Water → 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

HRID 50136

反応式

HRID 50136 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][C@H:13]1[CH2:17][NH:16][C@H:15]([C:18]([OH:20])=[O:19])[CH2:14]1.C([O-])(O)=O.[Na+].O>CC(C)=O>[OH:12][C@H:13]1[CH2:17][N:16]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[C@H:15]([C:18]([OH:20])=[O:19])[CH2:14]1

参加物

6

反応物 4

HCID 962WaterHCID 5810L-HydroxyprolineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

生成物 1

HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate収率 101.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Benzyl chloroformate (8.6 mL, 0.06 mol) was dissolved in acetone (12 mL), and this solution was added dropwise to a stirred solution of trans-4-Hydroxy-L-proline (6.56 g, 0.05 mol) in satd. NaHCO3 (160 mL) and H2O (24 mL). The resulting solution was stirred for 6 h at room temperature. The solution was washed with diethyl ether, and the organic layer was discarded. The aqueous layer was acidified with to pH 3 with 1 M HCl and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to afford 13.5 g (quantitative yield) of the desired product as an oil.

後処理

  1. washThe solution was washed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-9a1d1d93f4d949d09dae036b0adc2a31
出典データセット
uspto-grants-2004_03
特許番号
US06710186B2

関連ノート

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