Trifluoroacetic acid → HCID 86697210, compound

HRID 237547Notes

Reaction equation

HRID 237547 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([Br:18])=[C:13]([CH3:19])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[Br:18][C:14]1[C:13]([CH3:19])=[CH:12][C:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:16][C:15]=1[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86697211HCID 86697211, compound

Product 1

HCID 86697210HCID 86697210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N-di-tert.-butoxycarbonyl-2-(4-bromo-3,5-dimethylphenyl)ethanamine (1.19 g) in dichloromethane (25 mL) is added trifluoroacetic acid (320 μL). The mixture is stirred for 12 hours at room temperature. Then the mixture is partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is dried (MgSO4), the solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. Yield: 550 mg; LC (method 8): tR=0.68 min; Mass spectrum (ESI+): m/z=328 [M+H]+.

Workup

  1. customThen the mixture is partitioned between saturated aqueous NaHCO3 solution and dichloromethane
  2. dry with materialThe organic phase is dried (MgSO4)
  3. customthe solvent is evaporated
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-513cfd387fcd4cca98fbf909ab38826f
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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