Trifluoroacetic acid → HCID 178511564, compound

HRID 1671774Notes

Reaction equation

HRID 1671774 reaction equation
CC([N:5]([C@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:28])([F:27])[F:26])=[O:16])[CH2:11][CH2:10]1)C(=O)[O-])(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:5][C@@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:26])([F:27])[F:28])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178449842HCID 178449842, compound

Product 1

HCID 178511564HCID 178511564, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500 mL round bottom flask equipped with a magnetic stir bar was charged with 1,1-dimethylethyl{cis-4[({[2-(trifluoromethyl)phenyl]methyl}amino)carbonyl]cyclohexyl}carbamate (24.88 g, 62.1 mmol) and DCM (100 mL) at room temperature. Trifluoroacetic acid (100 mL) was added slowly, and the reaction was maintained at room temperature for 1 hour, before it was determined to be complete by LCMS (Retention time=5.71 min and m/e 301 [M+H]+). The volatiles were removed by rotary evaporation and the crude oil was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution (3×200 mL). The organic phase was dried over Na2SO4, filtered and concentrated to give 18.3 g of the title compound (60.9 mmol, 98%) as an off-white solid. MS (ES) m/e 301 [M+H]+.

Workup

  1. customA 500 mL round bottom flask equipped with a magnetic stir bar
  2. customThe volatiles were removed by rotary evaporation
  3. dissolutionthe crude oil was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution (3×200 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de38b1799be54aa3ad11bdb045177cec
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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