Hydrogen Bromide → 3-[3 (S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Hydrogen Bromide	HCID 260	—
Reactant	2-{[(Benzyloxy)(hydroxy)methylidene]amino}-N~1~-(4-{4-[(tert-butylimino)(hydroxy)methyl]-1,3-thiazolidin-3-yl}-3-hydroxy-1-phenylbutan-2-yl)butanediimidic acid	HCID 473592	—
Solvent	Acetic Acid	HCID 176	—
Solvent	Diethyl Ether	HCID 3283	—
Product	3-[3 (S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide	HCID 70040943	83.3%

Reaction Steps

A mixture of 170 mg of 3-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide and 0.3 ml of 32% (w/w) hydrogen bromide in glacial acetic acid was stirred at room temperature for 1 hour. The solution was diluted with diethyl ether and the precipitated solid was rapidly filtered off, washed with diethyl ether and dissolved in water. The solution was made alkaline by the addition of potassium carbonate and extracted with three portions of chloroform. The combined chloroform extracts were dried over anhydrous sodium sulphate, filtered and evaporated to give 110 mg of 3-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide; MS: m/e 466 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05620987
Source dataset	uspto-grants-1997_04
ORD ID	ord-7371b2b463264f9c8a35f66c7944e1a7
Source note	uspto-grants-1997_04