Acetic Acid → HCID 178511788, compound

HRID 64817Notes

Reaction equation

HRID 64817 reaction equation
C(O)(=O)C.Br.[CH2:6]([O:13][C:14](=[O:40])[C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20](=[O:39])[C@H:21]([CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)[NH:22]C(OCC1C=CC=CC=1)=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[CH2:6]([O:13][C:14](=[O:40])[C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20](=[O:39])[C@H:21]([CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)[NH2:22])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 178523868Nalpha-benzyloxycarbonyl-L-histidyl-L-proline benzyl ester

Product 1

HCID 178511788HCID 178511788, compoundYield 145%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

After ice-cooling 20 ml of an acetic acid solution of 25% hydrobromic acid, 1.91 g of compound (6) was added to the solution followed by reaction for 2 hours at 5°-10° C. The reaction mixture was added to 200 ml of dry ether and after quickly removing the precipitates thus formed by filtration and then the reaction mixture was dried overnight in a desiccator with potassium hydroxide, to provide 1.99 g of L-histidyl-L-proline benzyl ester.2-hydrobromide (7).

Workup

  1. additionwas added to the solution
  2. customfollowed by reaction for 2 hours at 5°-10° C
  3. customafter quickly removing the
  4. customprecipitates thus
  5. customformed by filtration
  6. dry with materialthe reaction mixture was dried overnight in a desiccator with potassium hydroxide

Sources & evidence

ORD record
ord-3af7a65dcd4e46779b89f2a557120a3c
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

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