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

HRID 1058276Notes

Reaction equation

HRID 1058276 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-cd20bbba88fa44fbafd3cd67e8bae55b
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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