Hydrochloric Acid → D-Phenylalanyl-N-[2-(ammoniomethyl)-5-chlorobenzyl]-L-prolinamide bis(hydrochloride)

HRID 1058339Notes

Reaction equation

HRID 1058339 reaction equation
[ClH:1].C(OCC([NH:10][C@@H:11]([C:19]([N:21]1[CH2:45][CH2:44][CH2:43][C@H:22]1[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[CH2:34][NH:35]C(OC(C)(C)C)=O)=[O:24])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C>C(OC(=O)C)C>[ClH:33].[ClH:1].[NH2:10][C@@H:11]([C:19]([N:21]1[CH2:45][CH2:44][CH2:43][C@H:22]1[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[CH2:34][NH3+:35])=[O:24])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69939891N-(tert-Butoxyacetyl)-D-phenylalanyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide

Product 1

HCID 86585777D-Phenylalanyl-N-[2-(ammoniomethyl)-5-chlorobenzyl]-L-prolinamide bis(hydrochloride)

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl gas was bubbled through a 0° C. solution of N-(tert-Butoxyacetyl)-D-phenylalanyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide (0.073 mmol, 45 mg) in 0.500 mL ethylacetate for 2 min. Let stir 1 h and concentrated in vaccuo to give D-Phenylalanyl-N-[2-(ammoniomethyl)-5-chlorobenzyl]-L-prolinamide bis(hydrochloride). Mass Spec ES (M+1)=415.1.

Workup

  1. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-307af15d8d82443aaa1a73556b37c987
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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