Trifluoroacetic acid → HCID 67235751, compound

HRID 1023523Notes

Reaction equation

HRID 1023523 reaction equation
CC([N:5]([C@H:9]([CH3:29])[C:10]([NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:28])[CH3:27])[CH:21]=2)=[CH:17][CH:18]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:28][CH:26]([C:22]1[CH:21]=[C:20]([O:19][C:16]2[N:15]=[CH:14][C:13]([NH:12][C:10](=[O:11])[C@@H:9]([CH3:29])[NH2:5])=[CH:18][CH:17]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673582HCID 86673582, compound2×

Product 1

HCID 67235751HCID 67235751, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,1-dimethylethyl{(1R)-1-methyl-2-[(6-{[3-(1-methylethyl)phenyl]oxy}-3-pyridinyl)amino]-2-oxoethyl}carbamate (Intermediate 25, 56 mg) was dissolved in 3 mL of dry dichloromethane. To this solution at 0° C. were added dropwise 30 equivalents of TFA (0.324 mL). The reaction was stirred at 0° C. for 3 hours. The reaction mixture was evaporated. The crude obtained was purified by SCX on a 5 g cartridge. 3 CV of methanol were used first, then the residue was adsorbed on the cartridge, washed with 5 CV of methanol and desorbed with 2 CV of methanolic ammonia (1N). Evaporation of the volatiles, afforded the title compound (38 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe crude obtained
  3. customwas purified by SCX on a 5 g cartridge
  4. washwashed with 5 CV of methanol
  5. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-3c109b9a4f804bd39d051d58ee48e14e
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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