Triethylamine → (3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917301노트

반응식

HRID 1917301 반응식
C(N(CC)CC)C.[C:8]([O:12][C:13]([C@@:15]1([CH2:29][CH2:30][OH:31])[CH2:19][C:18](=[O:20])[N:17]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].FC(F)(F)S(O[Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[C:8]([O:12][C:13]([C@@:15]1([CH2:29][CH2:30][O:31][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:19][C:18](=[O:20])[N:17]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 67491029HCID 67491029, 화합물

생성물 1

HCID 67490763(3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester수율 88%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Triethylamine (3.0 mL, 21.8 mmol) was added to a solution of (3S)-3-(2-hydroxyethyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.42 g, 7.25 mmol) in dichloromethane (70 mL), and the mixture was cooled to 0° C. tert-Butyldimethylsilyl trifluoromethanesulfonate (2.50 mL, 10.9 mmol) was added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. After addition of an ice piece and stirring, the reaction solution was poured into a mixture of ethyl acetate (50 mL) and saturated sodium bicarbonate (50 mL), followed by extraction with ethyl acetate (200 mL, 100 mL). The organic layers were combined and washed with brine (50 mL). After drying over anhydrous sodium sulfate and filtration, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1→2:1) to give 2.84 g (88%) of the title compound as a white solid.

후처리

  1. additionwas added dropwise
  2. stirringstirring
  3. extractionfollowed by extraction with ethyl acetate (200 mL, 100 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1→2:1)

출처 및 근거

ORD 기록
ord-af69ea3039714f8e9d8b70f371f870bb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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