HCID 54495310, compound → HCID 54561088, compound

HRID 2226602Notes

Reaction equation

C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:32])[N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Br:31])[CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:13]([C:33]([OH:35])=[O:34])[CH2:12]1)=O)C1C=CC=CC=1.C(OCC)(=O)C.C(O)CCC.C(OCC)(=O)C.O>Br.C(O)(=O)C>[Br:31][C:27]1[CH:26]=[C:25]([N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][C@H:13]2[C:33]([OH:35])=[O:34])=[O:32])[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A 2.13 g (3.96 mmole) portion of (S)-4-(benzyloxycarbonyl)-1-[N-(3-bromophenyl-N-phenylcarbamoyl]piperazine-2-carboxylic acid (from Step B) was dissolved in 40 ml of 30% HBr in acetic acid. After stirring for 1 hour at 25° C., the solution was flushed with nitrogen to remove the excess of HBr. Concentration in vacuo gave an oily residue which was partitioned between 100 ml of methylene chloride and 100 ml of water. The stirred slurry was neutralized to pH 7 with 10% NaOH solution. After a brief stirring the entire mixture was filtered to collect 1.50 g (3.71 mmole, 94%) of white solid which was homogeneous by TLC (5:1:1:1 ethyl acetate-n-butyl alcohol-ethyl acetate-water Rf =0.33).

Workup

customthe solution was flushed with nitrogen
customto remove the excess of HBr
concentrationConcentration in vacuo
customgave an oily residue which
customwas partitioned between 100 ml of methylene chloride and 100 ml of water
stirringAfter a brief stirring the entire mixture
filtrationwas filtered

Sources & evidence

ORD record: ord-a71a985ef6d745faa2a827afef2dec49
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348955

Reaction notes

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