Trifluoroacetic acid → (S,S)-2-(2-amino-4-methyl-pentylamino)-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide

HRID 278881Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]([CH2:13][NH:14][CH:15]([C:31](=[O:37])[NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:13][NH:14][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:22]=1)[C:31]([NH:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:37]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 850 mg (1.6 mmol) (1-{[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethylamino]-methyl}-3-methyl-butyl)-carbamic acid tert-butyl ester in 6 mL dichloromethane was treated with 2 mL 2,2,2-triflouroacetic acid and the resulting solution stirred 1 hour at 25° C. The mixture was concentrated at reduced pressure to a viscous amber oil to which was dissolved in 8 mL diethyl ether, and treated with 3 mL of diethyl ether which had been saturated with hydrogen chloride gas. The solvent was removed under reduced pressure, and the pale yellow oil thus obtained ((S,S)-2-(2-amino-4-methyl-pentylamino)-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide) was used directly in the next reaction.

Workup

concentrationThe mixture was concentrated at reduced pressure to a viscous amber oil to which
dissolutionwas dissolved in 8 mL diethyl ether
additiontreated with 3 mL of diethyl ether which
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-3c6b99b005fe40a58de1083a0fb44bc2
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362174B1

Reaction notes

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