Diisobutylaluminum hydride → 2,2-Bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester

HRID 1185675노트

반응식

HRID 1185675 반응식
CC(C[AlH]CC(C)C)C.[CH2:10]([O:17][C:18](=[O:44])[C:19]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:20][CH2:21][C:22](=[O:27])N(OC)C)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCCCCC>[CH2:10]([O:17][C:18](=[O:44])[C:19]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH2:20][CH2:21][CH:22]=[O:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 866488752,2-Bis(tert-butoxycarbonylamino)-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester

생성물 1

HCID 866488762,2-Bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester수율 75.2%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

A solution of DIBAL (1.0 M, 14.7 mL, 14.7 mmol) in hexane was added dropwise to a solution of 2,2-bis(tert-butoxycarbonylamino)-4-(methoxy-methyl-carbamoyl)-butyric acid benzyl ester (4 g, 10.5 mmol) under an atmosphere of nitrogen at −78° C. After 2 hours the mixture was quenched with saturated ammonium chloride (30 mL) and allowed to warm to room temperature. Water (20 mL) was added, and the mixture was extracted with diethyl ether (3×50 mL). The combined organic phases were left to stand at room temperature for 15 minutes. The resulting thick gel was filtered through a pad of CELITE. The filtrate was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to provide 2,2-bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester (3.34 g, 7.9 mmol, 75%). This was used immediately in the next step.

후처리

  1. customAfter 2 hours the mixture was quenched with saturated ammonium chloride (30 mL)
  2. additionWater (20 mL) was added
  3. extractionthe mixture was extracted with diethyl ether (3×50 mL)
  4. waitThe combined organic phases were left
  5. filtrationThe resulting thick gel was filtered through a pad of CELITE
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-2543ffcb19ea48cab9e71f436e806698
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669234B2

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