Acetic Acid → HCID 178511784, compound

HRID 64839Notes

Reaction equation

HRID 64839 reaction equation
C(OC([NH:11][C@H:12]([C:19]([N:21]1[CH2:34][CH2:33][CH2:32][C@H:22]1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=O)C1C=CC=CC=1.Br.C(O)(=O)C>CCOCC>[NH2:11][C@H:12]([C:19]([N:21]1[CH2:34][CH2:33][CH2:32][C@H:22]1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 178523864HCID 178523864, compound

Product 1

HCID 178511784HCID 178511784, compoundYield 161.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1.79 g of compound (95) was added 19 ml of 25% hydrobromic acid--acetic acid cooled in an ice bath followed by stirring one hour at room temperature. The reaction mixture was added to 190 ml of desiccator ether and precipitates thus formed were quickly collected by filtration and dried overnight in a desiccator containing potassium hydroxide to provide 2.05 g of L-histidyl-N-phenyl-L-prolinamide.2-hydrobromide (96).

Workup

  1. customprecipitates thus
  2. customformed
  3. filtrationwere quickly collected by filtration
  4. customdried overnight in a desiccator
  5. additioncontaining potassium hydroxide

Sources & evidence

ORD record
ord-71061dfacf2b46fa892634dba8e1b2cb
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

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