Trifluoroacetic acid → HCID 67235200, compound

HRID 1505352Notes

Reaction equation

HRID 1505352 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]([NH:21]C(=O)OC(C)(C)C)[CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[O:29][CH3:30].C(O)(C(F)(F)F)=O>ClCCl>[NH2:21][C@@H:18]([CH2:19][CH3:20])[C:16]([NH:15][C:12]1[CH:13]=[N:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:29][CH3:30])[CH:4]=2)=[CH:10][CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322503HCID 68322503, compound2×

Product 1

HCID 67235200HCID 67235200, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1-dimethylethyl ((1S)-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 66, 70 mg) in dichloromethane (2.5 mL) cooled down to 0° C. TFA (0.779 mL, 10.11 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 hours and then evaporated. The residue was diluted with dichloromethane (10 mL) and neutralized with a saturated aqueous solution of NaHCO3 (15 mL). The organic phase was separated, dried over sodium sulphate, filtered and evaporated to afford the title compound as a yellow pale oil (53.1 mg).

Workup

  1. customevaporated
  2. additionThe residue was diluted with dichloromethane (10 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d25ed34ff4a74e91b3b27dd08ac393c3
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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