Hydrochloric Acid → H-Val-Pro-Val-CF2CF2CF3.hydrochloride

HRID 613238Notes

Reaction equation

HRID 613238 reaction equation
[ClH:1].[NH:2](C(OC(C)(C)C)=O)[C@H:3]([C:7]([N:9]1[CH2:32][CH2:31][CH2:30][C@H:10]1[C:11]([NH:13][C@H:14]([C:18]([C:20]([C:23]([C:26]([F:29])([F:28])[F:27])([F:25])[F:24])([F:22])[F:21])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])=[O:8])[CH:4]([CH3:6])[CH3:5]>C(OCC)(=O)C>[NH2:2][C@H:3]([C:7]([N:9]1[CH2:32][CH2:31][CH2:30][C@H:10]1[C:11]([NH:13][C@H:14]([C:18]([C:20]([C:23]([C:26]([F:29])([F:27])[F:28])([F:24])[F:25])([F:21])[F:22])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])=[O:8])[CH:4]([CH3:5])[CH3:6].[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 131721521Boc-Val-Pro-Val-CF2CF2CF3

Product 1

HCID 131721523H-Val-Pro-Val-CF2CF2CF3.hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Bubble HCl gas into a stirred solution of Boc-Val-Pro-Val-CF2CF2CF3 (0.21 g, 0.37 mmol) in ethyl acetate (50 mL) and cool in an ice water bath. Treat with hydrogen chloride gas for 4 minutes. Stir the reaction mixture for 1 hour and warm to ambient temperature. Concentrate the reaction mixture and azeotrope with CCl4. Place under a high vacuum to give the title compound as a white solid. (Yield: 185 mg, 100%).

Workup

  1. temperaturecool in an ice water bath
  2. concentrationConcentrate the reaction mixture and azeotrope with CCl4

Sources & evidence

ORD record
ord-236cdb21c8384b2e8179f6a9c4a439df
Source dataset
uspto-grants-1999_12
Patent number
US06008196

Reaction notes

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