Acetic Acid → tert-Butyl [(3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl]carbamate

HRID 1511452

반응식

HRID 1511452 반응식
[CH:1]1([N+:4]#[C-:5])[CH2:3][CH2:2]1.[O:6]=[CH:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH3:11].C(O)(=[O:22])C>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:22])[CH:7]([OH:6])[C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH3:11])[CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 2758008IsocyanocyclopropaneHCID 10262225Carbamic acid, [(1S)-1-formylbutyl]-, 1,1-dimethylethyl ester (9CI)

생성물 1

HCID 56604963tert-Butyl [(3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl]carbamate수율 88.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

To a solution of cyclopropylisonitrile (1.91 g, 28.5 mmol), (S)-tert-butyl 1-oxopentan-2-ylcarbamate (3.8 g, 19 mmol) in methylene chloride (100 mL) was added acetic acid (2.28 g, 38 mmol) at 0° C. After the addition was complete the reaction mixture was allowed to warm to 25° C. and stirred for 6 hours. The reaction mixture was diluted with ethyl acetate (200 mL), then washed with a saturated solution of sodium bicarbonate and brine (30 mL) and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was crystallized from 50 mL of ethyl acetate and hexane(v/v=1/1) to give tert-butyl (3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamate (4.8 g) as a white solid.

후처리

  1. additionAfter the addition
  2. washwashed with a saturated solution of sodium bicarbonate and brine (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was crystallized from 50 mL of ethyl acetate and hexane(v/v=1/1)

출처 및 근거

ORD 기록
ord-8b8843b3851a4d78b8d746d1c3319784
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211897B2

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