Trifluoroacetic acid → HCID 66733097, compound

HRID 241690Notes

Reaction equation

HRID 241690 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])=O)(C)(C)C.[C:23](O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)[C:12]([O:14][CH2:15][CH3:23])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66733461HCID 66733461, compound

Product 1

HCID 66733097HCID 66733097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-(tert.-butoxycarbonylamino)-5-tert-butylbenzoate (0.42 g) was dissolved in DCM (5 ml). To the resulting solution, TFA (1 ml) was added, the mixture was stirred for 30 min at room temperature and then concentrated in vacuum. The residue was dissolved in DCM and extracted with aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulphate and concentrated in vacuum to yield ethyl 3-amino-5-tert-butylbenzoate (0.28 g), which was used for the synthesis of example 112 without further purification.

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue was dissolved in DCM
  3. extractionextracted with aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0a61f5c48079454ba2420f127f346d2e
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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