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1,2-Dichloroethane → N-(tert-buyloxycarbonyl)-D-phenylalanyl-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide

HRID 1058276
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HRID 1058276 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:11]=1[CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[NH:23]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@@H:24]([C:32]([N:34]1[CH2:41][CH2:40][CH2:39][C@H:35]1[C:36](O)=[O:37])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=NC2N(O)N=NC=2C=1>CN(C)C=O>[C:45]([O:44][C:42]([NH:23][C@@H:24]([C:32]([N:34]1[CH2:41][CH2:40][CH2:39][C@H:35]1[C:36]([NH:13][CH2:12][C:11]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:10]=1[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:37])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:43])([CH3:48])([CH3:46])[CH3:47]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 1797945Boc-D-phe-pro-OHHCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

생성물 1

HCID 69975973N-(tert-buyloxycarbonyl)-D-phenylalanyl-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of 2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamine from the previous step (0.14 mmol, 37 mg), EDC (0.21 mmol, 40 mg), and Boc-D-Phe-L-Pro-OH (0.14 mmol, 50 mg), in 0.5 mL dimethylformamide, was added HOAT (0.15 mmol, 21 mg). The solution was stirred overnight and purified by preparative reverse phase HPLC using an acetonitrile:water gradient containing 0.1% TFA to give N-(tert-buyloxycarbonyl)-D-phenylalanyl-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide. Mass Spec ES (M+1)=615.2.

후처리

  1. custompurified by preparative reverse phase HPLC
  2. additionwater gradient containing 0.1% TFA

출처 및 근거

ORD 기록
ord-cd20bbba88fa44fbafd3cd67e8bae55b
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06515011B2

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