HCID 18965166, compound → HCID 54561088, compound

HRID 486753Notes

Reaction equation

HRID 486753 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)[CH: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

5

Reactant 2

HCID 18965166HCID 18965166, compoundHCID 86747645HCID 86747645, compound

Product 1

HCID 54561088HCID 54561088, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

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

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

Sources & evidence

ORD record
ord-ae080796a13d45f7880b704717902b8c
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Reaction notes

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