Trifluoroacetic acid → Trifluoroacetate

HRID 529521Notes

Reaction equation

HRID 529521 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9]C(=O)OC(C)(C)C)[CH2:7][CH:6]=[CH:5][CH2:4][N:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>C(Cl)Cl>[NH2:9][C@H:8]1[CH2:7][CH:6]=[CH:5][CH2:4][N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:2]1=[O:1].[F:26][C:25]([F:28])([F:27])[C:23]([O-:29])=[O:24]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68292809(S,Z)-tert-butyl 2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Product 2

HCID 84468TrifluoroacetateYield 98%HCID 68292370(S,Z)-3-amino-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added (S,Z)-tert-butyl 2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (85 mg, 0.28 mmol), DCM (1 mL) and TFA (1 mL). The reaction mixture was stirred at rt for 2 hr. The reaction mixture was concentrated and dried under high vacuum for 1 h to afford (S,Z)-3-amino-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one, trifluoroacetate (87 mg, 0.28 mmol, 98% yield) as an oil. Anal. Calcd. for C12H14N2O m/z 202.2. found: 203.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under high vacuum for 1 h

Sources & evidence

ORD record
ord-cfc21c62d78640aa928ad5fd8660c5ae
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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