Trifluoroacetic acid → HCID 67235584, compound

HRID 1505374Notes

Reaction equation

HRID 1505374 reaction equation
[CH3:1][C@:2]([NH:24]C(=O)OC(C)(C)C)([C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[CH:12][CH:13]=1)=[O:6])[CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:11]2[N:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C@:2]([CH3:1])([CH2:3][CH3:4])[NH2:24])=[CH:13][CH:12]=2)=[CH:16][C:17]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89843282HCID 89843282, compound2×

Product 1

HCID 67235584HCID 67235584, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl ((1R)-1-methyl-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 98, 65 mg) in dry dichloromethane (3 mL) cooled to 0° C., TFA (0.700 mL, 9.08 mmol) was added dropwise. The reaction was stirred at that temperature for 2 hours. The reaction was quenched with a saturated aqueous solution of NaHCO3 (20 mL) added at 0° C., and extracted with dichloromethane (3×7 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound as a white solid (44 mg).

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of NaHCO3 (20 mL)
  2. additionadded at 0° C.
  3. extractionextracted with dichloromethane (3×7 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-41cb245c405245d094930ba9cc27cf8f
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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