Tert-butyl 2,2,2-trichloroethanimidate → tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-hydroxypropanoate

HRID 1776967

반응식

HRID 1776967 반응식
[C:1]([NH:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][OH:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].ClC(Cl)(Cl)C(=N)O[C:29]([CH3:32])([CH3:31])[CH3:30]>CCOC(C)=O.C1CCCCC1>[CH:7]1[C:6]2[CH:5]([CH2:4][O:3][C:1]([NH:18][CH:19]([CH2:20][OH:21])[C:22]([O:24][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:23])=[O:2])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

참가 물질

5

반응물 2

HCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 6541433(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoic acid

생성물 1

HCID 13965220tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-hydroxypropanoate수율 68.3%

시약·촉매·용매 2

HCID 8078Cyclohexane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of commercial N-Fmoc-L-serine (1.5 g, 4.58 mmol) in EtOAc (40 ml), a solution of t-butyl 2,2,2-trichloroacetimidate (4.00 g, 18.32 mmol) in cyclohexane (18 ml) was added dropwise. After stirring at room temperature for 24 hrs, the solution was evaporated and the residue was purified by flash chromatography (n-Hexane/EtOAc 70:3), yielding the title compound (1.20 g, 68%).

후처리

  1. customthe solution was evaporated
  2. customthe residue was purified by flash chromatography (n-Hexane/EtOAc 70:3)

출처 및 근거

ORD 기록
ord-28932fd93c5d4c7dbdb19f8ffbd9edea
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266820B2

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