Water → 3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-3-oxopropionic acid ethyl ester

HRID 35871ノート

反応式

HRID 35871 の反応式
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH2:14][CH2:15][C:16](=[O:26])[N:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])[OH:7])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.O>CC(C)=O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH2:14][CH2:15][C:16](=[O:26])[N:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])=[O:7])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 3776IsopropanolHCID 15660989(3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl esterHCID 131709961Jones' reagent

生成物 1

HCID 156609903-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-3-oxopropionic acid ethyl ester収率 42.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of (3RS)-3-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propionyl]pyrrolidin-2-yl]-3-hydroxypropionic acid ethyl ester (230 mg) in acetone (1 ml) was cooled to -30° C. Excess Jones' reagent was added dropwise to the solution. The mixture was stirred for 1 hr at the same temperature, and for 1 hr at -20° C., and for 1 hr at -10° C. Isopropyl alcohol was added to the reaction solution. Water was added to the mixture. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (98 mg) having the following physical data:

後処理

  1. waitfor 1 hr at -20° C.
  2. waitfor 1 hr at -10° C
  3. extractionThe mixture was extracted with EtOAc
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

出典と根拠

ORDレコード
ord-df35b2df9c34402fb24e1439996fd691
出典データセット
uspto-grants-1995_05
特許番号
US05411974

反応ノート

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