Hydrogen Bromide → HCID 178513920, compound

Participants

Reaction Steps

A solution of 30% hydrogen bromide in acetic acid (4.0 ml) was added to (2S)-2-[[(2S)-2-benzyloxycarbonylamino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]propionic acid (772 mg) in an ice-water bath. The mixture was stirred for 15 minutes and then additional portion (4.0 ml) of a solution of hydrogen bromide in acetic acid was added thereto at ambient temperature. The mixture was stirred for 2.5 hours, and poured into a mixture of ice-water (25 ml) and ethyl acetate (25 ml). The aqueous layer was separated and then the remaining organic layer was extracted with water (30 ml). The aqueous layer were combined and subjected to a column of Dowex 50W x 8 (H30 , 20 ml) and the elution was carried out with water (200 ml) and 1.4% aqueous ammonia (250 ml). The fractions containing the object compound were combined and evaporated in vacuo. The residue was dissolved in water (30 ml) and filtered. The filtrate was lyophilized to give a white powder (315 mg) of (2S)-2-[[(2S)-2-amino-3-carbamoylpropionyl]amino]-3-[[(1S)-1-carboxy-2-(4-imidazolyl)ethyl]amino]propionic acid.

Provenance & Evidence