Trifluoroacetic acid → HCID 67235810, compound

HRID 1505355Notes

Reaction equation

HRID 1505355 reaction equation
[CH3:1][C:2]([NH:22]C(=O)OC(C)(C)C)([CH3:21])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:8][CH:7]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:21][C:2]([C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:8][CH:7]=1)=[O:4])([CH3:1])[NH2:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71006805HCID 71006805, compound2×

Product 1

HCID 67235810HCID 67235810, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {1,1-dimethyl-2-[(4-{[3-(methyloxy)phenyl]oxy}phenyl)amino]-2-oxoethyl}carbamate (Intermediate 71, 1.89 g) in dry dichloromethane (60 mL) at 0° C. TFA (20 mL, 260 mmol) was added dropwise and the reaction mixture was stirred for 2 hours at the same temperature. The solvent and the excess of TFA were evaporated and the residue was purified by SCX cartridge (50 g) to afford the title compound as a light brown oil (1.34 g).

Workup

  1. customat 0° C
  2. customThe solvent and the excess of TFA were evaporated
  3. customthe residue was purified by SCX cartridge (50 g)

Sources & evidence

ORD record
ord-dfe3dcb9eda6495688d95b73e9d6b093
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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