Trifluoroacetic acid → HCID 66733097, compound

HRID 1422406Notes

Reaction equation

HRID 1422406 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-621cc250a12749e2ad2a403d76975118
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

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