Hydrochloric Acid → HCID 14503296, compound

HRID 366941Notes

Reaction equation

HRID 366941 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3](=[O:33])[CH:4]([NH:8][C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@H:16]([CH3:30])[NH:17][C:18](=[O:29])[C@H:19]([CH3:28])[NH:20]C(OC(C)(C)C)=O)[CH:5]([CH3:7])[CH3:6].Cl>C(OCC)(=O)C>[F:35][C:2]([F:1])([F:34])[C:3](=[O:33])[CH:4]([NH:8][C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@H:16]([CH3:30])[NH:17][C:18](=[O:29])[C@H:19]([CH3:28])[NH2:20])[CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10791750HCID 10791750, compound

Product 1

HCID 14503296HCID 14503296, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,1,1-Trifluoro-3[(N-tert-butyloxycarbonylalanyl)alanyl-prolylamino]-4-methylpentan-2-one (180 mg, 0.35 mmol) in ethyl acetate (50 ml) was cooled to 0° C. and treated with hydrogen chloride gas for 5 min. The reaction mixture was stirred at 0° C. for 1.5 hr, followed by removal of solvent in vacuo. 1,1,1-Trifluoro-3-[alanylalanylprolylamino]-4-methylpentan-2-one (151 mg, 0.34 mmol) was obtained in 96% yield and was used for subsequent reactions without purification.

Workup

  1. customfollowed by removal of solvent in vacuo

Sources & evidence

ORD record
ord-709de3788c954092995041f11e249efa
Source dataset
uspto-grants-2000_10
Patent number
US06130315

Reaction notes

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