Methanol → Z-Trp-ome

HRID 1500156

반응식

HRID 1500156 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:23]([OH:25])=[O:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[CH2:28]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:28][O:24][C:23](=[O:25])[C@H:12]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

참가 물질

6

반응물 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 101176benzyloxycarbonyl-L-tryptophan

생성물 1

HCID 11256670Z-Trp-ome

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred suspension of (S)—N-benzyloxycarbonyl-L-tryptophan 1a (2.45 g, 7.2 mmol) in 10 ml anhydrous CH2Cl2, was added DMAP (0.1 g, 0.82 mmol) and methanol (0.28 g, 11.8 mmol). At 0° C., DCC in CH2Cl2 solution was slowly added to the mixture and then it was allowed to warm to room temperature and stirred overnight. After twice filtration and evaporation, the residue was purified by flash column chromatography (n-hexane/EA, 4:1 to 2:1) and afforded the desired product (S)-2a as a colourless oil (2.5 g, 98%).

후처리

  1. filtrationAfter twice filtration and evaporation
  2. customthe residue was purified by flash column chromatography (n-hexane/EA, 4:1 to 2:1)

출처 및 근거

ORD 기록
ord-9c66da0efff34c8aba0596e2e03199c5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206090B2

연결된 노트

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