Ethyl 2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoate → N-(Benzyloxycarbonyl)-3,3,3-trifluoroalanine ethyl ester

HRID 58899노트

반응식

HRID 58899 반응식
[CH2:1]([O:8][C:9]([N:11]=[C:12]([C:18]([F:21])([F:20])[F:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:18]([F:19])([F:21])[F:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 2758803Ethyl 2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoateHCID 4311764Sodium borohydride

생성물 1

HCID 562278N-(Benzyloxycarbonyl)-3,3,3-trifluoroalanine ethyl ester수율 48.5%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of ethyl 2-(benzyloxycarbonylimino)-3,3,3-trifluoropropanoate (45.0 g, 148.5 mmol) in diethyl ether (300 mL) was added sodium borohydride (11.3 g 297 mmol) in portions at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The reaction was quenched with water (100 mL) carefully and the organic layer was separated. The aqueous layer was extracted with EtOAc (100 mL×3). The organic layers were combined, washed with brine (200 mL×2), dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether=1:9) to afford ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoropropanoate (22.0 g, 48% yield).

후처리

  1. customThe reaction was quenched with water (100 mL) carefully
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc (100 mL×3)
  4. washwashed with brine (200 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel (EtOAc/petroleum ether=1:9)

출처 및 근거

ORD 기록
ord-9415beac30574252947e509ec9035b64
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434761B2

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