Trifluoroacetic acid → (2S)-2-amino-3-biphenyl-4-yl-N,N-dimethylpropanamide

HRID 449487Notes

Reaction equation

HRID 449487 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@@H:15]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])(C)(C)C>C(Cl)Cl>[NH2:14][C@@H:15]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:26][CH:27]=1)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59496665tert-butyl[(1S)-1-(biphenyl-4-ylmethyl)-2-(dimethylamino)-2-oxoethyl]carbamate

Product 1

HCID 59496687(2S)-2-amino-3-biphenyl-4-yl-N,N-dimethylpropanamideYield 130.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL, 10 mmol) was added to a solution of tert-butyl[(1S)-1-(biphenyl-4-ylmethyl)-2-(dimethylamino)-2-oxoethyl]carbamate (50 mg, 0.1 mmol) in methylene chloride (2 mL). The reaction was stirred for 2 h., and was concentrated under reduced pressure to give the crude product (2S)-2-amino-3-biphenyl-4-yl-N,N-dimethylpropanamide (35 mg, 97%). Analytical LCMS (M+H)+: m/z=269.0.

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-83527e98f00f466188651e6b1fdceb05
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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