Acetic Acid Mixture with Hydrobromic Acid → HCID 57210532, compound

HRID 1033856Notes

Reaction equation

HRID 1033856 reaction equation
C([O:8][C:9]([C:11]1[N:12]=[CH:13][S:14][C:15]=1[CH2:16][CH2:17][NH:18][C:19](=[O:43])[C@H:20]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:21][C@H:22]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:10])C1C=CC=CC=1.Br.C(O)(=O)C>>[C:9]([C:11]1[N:12]=[CH:13][S:14][C:15]=1[CH2:16][CH2:17][NH:18][C:19](=[O:43])[C@H:20]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:21][C@H:22]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([OH:10])=[O:8]

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 57305755HCID 57305755, compound

Product 1

HCID 57210532HCID 57210532, compoundYield 67.9%

Procedure

A mixture of 2.2 g of 4-benzyloxycarbonyl-5-{2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)-(L)-phenylalanyl]aminoethyl}thiazole and 30 ml of a 25% hydrogen bromide-acetic acid solution was stirred at room temperature for one day. After removing the solvent, the mixture was neutralized with a 10% potassium carbonate aqueous solution. The crystals obtained were recrystallized from a methanol-isopropyl ether mixed solution to obtain 1.27 g of 4-carboxy-5-{2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)-(L)-phenylalanyl]aminoethyl}thiazole.

Workup

  1. customAfter removing the solvent
  2. customThe crystals obtained
  3. customwere recrystallized from a methanol-isopropyl ether mixed solution

Sources & evidence

ORD record
ord-7fab03614aed494cb22fe6847856988f
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

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