1,2-Dichloroethane → N-(tert-Butoxyacetyl)-D-phenylalanyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide

HRID 1058338Notes

Reaction equation

HRID 1058338 reaction equation
[NH2:1][CH2:2][C:3]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:4]=1[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH2:19](Cl)CCl.[NH:23]([C:42]([O:44]C(C)(C)C)=O)[C@@H:24]([C:32]([N:34]1[CH2:41][CH2:40][CH2:39][C@H:35]1[C:36]([OH:38])=O)=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=N[C:52]2N(O)N=N[C:51]=2[CH:50]=1.CN(C)[CH:61]=[O:62]>>[C:51]([O:62][CH2:61][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:1][CH2:2][C:3]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:4]=1[CH2:5][NH:6][C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:13])=[O:38])=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:44])([CH3:50])([CH3:52])[CH3:19]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 181649HOAtHCID 1797945Boc-D-phe-pro-OHHCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

Product 1

HCID 69939891N-(tert-Butoxyacetyl)-D-phenylalanyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide

Procedure

To a solution of tert-Butyl 2-(aminomethyl)-4-chlorobenzylcarbamate (0.14 mmol, 37 mg), EDC (0.21 mmol, 40 mg), and Boc-D-Phe-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 prep HPLC to give N-(tert-Butoxyacetyl)-D-phenylalanyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide. Mass Spec ES (M+1)=615.2.

Workup

  1. custompurified by prep HPLC

Sources & evidence

ORD record
ord-2ed7789c584847d9a31369e434f6a513
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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