Dimethyl Sulfoxide → (3S)-3-(3-Oxo-1-propyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917403노트

반응식

HRID 1917403 반응식
C(=O)=O.CO.C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:16]([O:20][C:21]([C@@:23]1([CH2:37][CH2:38][CH2:39][OH:40])[CH2:27][C:26](=[O:28])[N:25]([C@@H:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:30])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[C:16]([O:20][C:21]([C@@:23]1([CH2:37][CH2:38][CH:39]=[O:40])[CH2:27][C:26](=[O:28])[N:25]([C@@H:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:30])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

참가 물질

8

반응물 6

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 21973728Carbon dioxide methanolHCID 67491012(3S)-3-(3-hydroxy-1-propyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 86664654(3S)-3-(3-Oxo-1-propyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester수율 100.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dichloromethane (35 ml) was cooled with dry ice-methanol in a nitrogen atmosphere. Oxalyl chloride (3.45 ml, 39.5 mmol) and dimethyl sulfoxide (4.68 ml, 66.0 mmol) were added, and the mixture was stirred under cooling for 15 minutes. A solution of (3S)-3-(3-hydroxy-1-propyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (4.58 g, 13.2 mmol) in dichloromethane (31 mL) was added, and the mixture was stirred under cooling for one hour. Triethylamine (11.1 ml, 79.5 mmol) was added under cooling, and the mixture was stirred under cooling for one hour and then at room temperature for one hour. A saturated ammonium chloride solution (100 ml) was added to the reaction solution, followed by extraction with chloroform (100 ml×1, 80 ml×1). The organic layer was washed with brine (120 ml) and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→66:34→60:40→50:50→40:60→34:66→25:75) to give 4.59 g of the title compound as white crystals.

후처리

  1. temperatureunder cooling for 15 minutes
  2. stirringthe mixture was stirred
  3. temperatureunder cooling for one hour
  4. temperatureunder cooling
  5. stirringthe mixture was stirred
  6. temperatureunder cooling for one hour
  7. extractionfollowed by extraction with chloroform (100 ml×1, 80 ml×1)
  8. washThe organic layer was washed with brine (120 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→66:34→60:40→50:50→40:60→34:66→25:75)

출처 및 근거

ORD 기록
ord-7cc9a4cf453d45d99927985d35ed6fbe
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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