Hydrochloric Acid → (3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl ester

HRID 344703노트

반응식

HRID 344703 반응식
II.Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([N:17]([CH3:31])[C:18]([CH2:20][CH2:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH:29]=[O:30])=[O:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C1COCC1.C1C=CC=CC=1.[Zn]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH:29]([C@@H:25]1[CH2:26][CH2:27][CH2:28][N:24]1[C:22](=[O:23])[CH2:21][CH2:20][C:18](=[O:19])[N:17]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:31])[OH:30])[CH3:9]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al

생성물 1

HCID 15660989(3RS)-3-[(2S)-1-(3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl)-3-hydroxypropionic acid ethyl ester

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 241Benzene용매HCID 8028Tetrahydrofuran용매

실험 절차

Zinc powder (482 mg) and a small amount of iodine were added to a solution of ethyl bromoacetate (0.70 ml) in THF (6 ml). The mixture was refluxed for 30 mins. The solution was added dropwise to a solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (1.21 g) in benzene (10 ml). The mixture was refluxed for 30 mins. After reaction, 1N hydrochloric acid 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 (1.21 g) having the following physical data:

후처리

  1. temperatureThe mixture was refluxed for 30 mins
  2. temperatureThe mixture was refluxed for 30 mins
  3. additionwas added to the mixture
  4. extractionThe mixture was extracted with EtOAc
  5. washThe extract was washed
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

출처 및 근거

ORD 기록
ord-b30ad46a94c54985b6aecece104c43f9
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053414

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