Trifluoroacetic acid → HCID 67235200, compound

HRID 1023553Notes

Reaction equation

HRID 1023553 reaction equation
CC([N:5]([C@H:9]([C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([O:29][CH3:30])[CH:23]=2)=[CH:19][CH:20]=1)=[O:13])[CH2:10][CH3:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:5][C@@H:9]([CH2:10][CH3:11])[C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([O:29][CH3:30])[CH:23]=2)=[CH:19][CH:20]=1)=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673593HCID 86673593, compound2×

Product 1

HCID 67235200HCID 67235200, compoundYield 99.7%

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 dichlorometane (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-b527e0293aba4f9f815d88c612abae1f
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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