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Dicyclohexylcarbodiimide → N2 [3(S)-[N-(benzyloxycarbonyl)-L-asparaginylamino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(R)-hydroxy-L-prolinamide

HRID 466882
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HRID 466882 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=[N:27][NH:26]C=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.N#N.[NH2:47][C@@H:48]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C@H:49]([OH:64])[CH2:50][C@@:51]1([C:61]([NH2:63])=[O:62])[CH2:55][C@@H:54]([OH:56])[CH2:53][N:52]1[C:57]([CH3:60])([CH3:59])[CH3:58]>ClCCl.CO>[N:26]#[N:27].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:47][C@@H:48]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C@H:49]([OH:64])[CH2:50][C@@:51]1([C:61]([NH2:63])=[O:62])[CH2:55][C@@H:54]([OH:56])[CH2:53][N:52]1[C:57]([CH3:60])([CH3:58])[CH3:59])=[O:19])[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 75314Benzyloxycarbonyl-asparagineHCID 86746268HCID 86746268, 화합물HCID 178418300HCID 178418300, 화합물

생성물 1

HCID 86746266N2 [3(S)-[N-(benzyloxycarbonyl)-L-asparaginylamino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(R)-hydroxy-L-prolinamide수율 37.7%

시약·촉매·용매

2
HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

In a manner analogous to that described in Example 92, from 0.133 g of N-(benzyloxycarbonyl)-L-asparagine, 0.068 g of hydroxybenzotriazole, 0.103 g of dicyclohexylcarbodiimide and 0.16 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide, but using dichloromethane in place of ethyl acetate as the partitioning solvent and 20% methanol in dichloromethane for the chromatography and carrying out the re-evaporation with diethyl ether, there was obtained 0.1 g of N2 -[3(S)-[N-(benzyloxycarbonyl)-L-asparaginylamino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide of melting point 115° C.

후처리

  1. customthe re-evaporation with diethyl ether

출처 및 근거

ORD 기록
ord-f97da7e997304b4c9c41c21704de0da6
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05157041

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