4-Methylmorpholine → tert-Butyl (S)-(1-amino-1-oxobutan-2-yl)carbamate

HRID 1670665노트

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HRID 1670665 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:16]1CCOCC1.ClC(OCC(C)C)=O.[NH4+].[OH-]>CN(C=O)C.CCCCCC>[C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH3:14])(=[O:11])[NH2:16]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acid

생성물 1

HCID 45092008tert-Butyl (S)-(1-amino-1-oxobutan-2-yl)carbamate수율 80.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

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온도
-20 °C

실험 절차

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]butanoic acid (1.01 g, 4.99 mmol) in DMF (5 mL) at −20° C. was added NMM (1.10 mL, 9.99 mmol) and isobutyl chloroformate (1.30 mL, 9.99 mmol). The reaction was stirred for 10 min at −20° C. The precipitate was removed by filtration. 26% NH4OH (aq) solution (0.39 mL, 9.99 mmol) was added and the reaction was stirred at −20° C. for 3 h. The volume was reduced under vacuum and hexane was added. A white precipitate was formed after a few minutes. The precipitate was collected in a filter and washed with additional hexane. The precipitate was recrystallised from EtOAc and hexane to give the title compound (0.811 g, 80%) as white solid.

후처리

  1. customThe precipitate was removed by filtration
  2. stirringthe reaction was stirred at −20° C. for 3 h
  3. additionwas added
  4. customA white precipitate was formed after a few minutes
  5. customThe precipitate was collected in
  6. filtrationa filter
  7. washwashed with additional hexane
  8. customThe precipitate was recrystallised from EtOAc and hexane

출처 및 근거

ORD 기록
ord-7d703dc4287e4864911fcbe1f573466d
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994179B2

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