Dicyclohexylcarbodiimide → 13-(S)-[[(9H-Fluoren-9-yl)methoxycarbonyl]amino]-3-(R)-methyl-12-oxo-14-(phenylmethoxy)-6-(phenylmethyl)-2,6,11-triazatetradecanoic acid, 1,1-dimethylethyl ester

HRID 1418623노트

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HRID 1418623 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:29](O)=[O:30])[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:57][CH2:58][CH2:59][CH2:60][CH2:61][N:62]([CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[CH2:63][CH2:64][C@H:65]([NH:67][C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71])[CH3:66]>ClCCl.C(OCC)(=O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:20][O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:29](=[O:30])[NH:57][CH2:58][CH2:59][CH2:60][CH2:61][N:62]([CH2:75][C:76]3[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=3)[CH2:63][CH2:64][C@@H:65]([CH3:66])[NH:67][C:68]([O:69][C:70]([CH3:73])([CH3:71])[CH3:72])=[O:74])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7017914Fmoc-O-benzyl-L-serineHCID 10689168N-[3-[(4-aminobutyl)(phenylmethyl)amino]-1-(R)-methylpropyl]carbamic acid, 1, 1-dimethylethyl ester

생성물 1

HCID 8675393313-(S)-[[(9H-Fluoren-9-yl)methoxycarbonyl]amino]-3-(R)-methyl-12-oxo-14-(phenylmethoxy)-6-(phenylmethyl)-2,6,11-triazatetradecanoic acid, 1,1-dimethylethyl ester수율 96.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

1.71 g (4.1.10-3 mol) of N-[(9H-fluoren-9-yl)methoxycarbonyl]-O-phenylmethyl-(L)-serine are dissolved in 60 ml of dichloromethane. The solution is cooled to 0° C. and a solution of 0.55 g (4.10-3 mol) of HOBT and 1.54 g (7.5.10-3 mol) of DCC in 20 ml of dichloromethane is added. The mixture is stirred for 0.5 hour, 1.30 g (3.72.10-3 mol) of N-[3-[(4-aminobutyl)(phenylmethyl)amino]-1-(R)-methylpropyl]carbamic acid, 1, 1-dimethylethyl ester are then added and the reaction mixture is stirred at room temperature for 16 hours. The solvent is removed under reduced pressure and the residue is purified by chromatography on silica gel using an ethyl acetate/methylcyclohexane mixture (1/1 v/v) and then pure ethyl acetate as the eluent to give 2.7 g of the expected product in the form of a white crystalline solid (yield=96%).

후처리

  1. stirringthe reaction mixture is stirred at room temperature for 16 hours
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is purified by chromatography on silica gel using an ethyl acetate/methylcyclohexane mixture (1/1 v/v)

출처 및 근거

ORD 기록
ord-783bf9f57d18491b950657b284592a9c
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883132

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