Benzylamine → N-benzyl-O-benzyl-N2-Boc-D-serinamide

HRID 534673

반응식

HRID 534673 반응식
[C:1]([NH:8][C@@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl.C(N(CC)CC)C>[CH2:22]([NH:29][C:19](=[O:21])[C@@H:9]([CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 2

HCID 7504BenzylamineHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

생성물 1

HCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide수율 41%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

To a cooled (−20° C.) solution of N-Boc-O-benzyl-D-serine (1 g) in dichloro methane (12 mL), triethylamine (0.44 mL) was added and stirred for 5 minutes and subsequently isobutylchloformate (0.51 mL) was added to the reaction mixture in 5 minutes at −20° C. The solution was stirred for 5 minutes at −20° C. and benzyl amine (0.44 mL) was added to in it in 5 minutes at −20° C. The solution was stirred for 1 hr at −20° C. The solution was allowed to warm to room temperature and stirred for 1 hour. The hydrochloride salt of N-methylmorpholine was filtered. Organic layer was concentrated under vacuum to obtain solid, 0.53 g N-benzyl-O-benzyl-N2-Boc-D-serinamide after crystallization by diisopropylether.

후처리

  1. additionwas added
  2. additionsubsequently isobutylchloformate (0.51 mL) was added to the reaction mixture in 5 minutes at −20° C
  3. stirringThe solution was stirred for 5 minutes at −20° C.
  4. stirringThe solution was stirred for 1 hr at −20° C
  5. stirringstirred for 1 hour
  6. filtrationThe hydrochloride salt of N-methylmorpholine was filtered
  7. concentrationOrganic layer was concentrated under vacuum

출처 및 근거

ORD 기록
ord-434591b48bc24c069a730e5fabdc54e4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853439B2

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