Trifluoroacetic acid → HCID 70869014, compound

HRID 1505353Notes

Reaction equation

HRID 1505353 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([O:10][C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18]([C@H:20]([NH:23]C(=O)OC(C)(C)C)[CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].C(O)(C(F)(F)F)=O>ClCCl>[NH2:23][C@H:20]([CH2:21][CH3:22])[C:18]([NH:17][C:14]1[CH:15]=[N:16][C:11]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=2)=[CH:12][CH:13]=1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71006878HCID 71006878, compound2×

Product 1

HCID 70869014HCID 70869014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,1-dimethylethyl ((1R)-1-{[(6-{[3-(1-methylethyl)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 69, 1.28 g) was dissolved in 18 mL of dry dichloromethane. To this solution at 0° C. under argon was added dropwise 30 equivalents of TFA (7.15 mL, 93 mmol). The reaction was stirred during 3 hours at 0° C. The reaction mixture was evaporated. The residue obtained was purified by SCX on a 50 g cartridge. The cartridge was washed with 3 CV of methanol, then the compound was adsorbed on the cartridge, washed with 5 CV of methanol and desorbed with 2 CV of methanolic ammonia (1N). After evaporation of the volatiles, the title compound was obtained (932 mg).

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue obtained
  3. customwas purified by SCX on a 50 g cartridge
  4. washThe cartridge was washed with 3 CV of methanol
  5. washwashed with 5 CV of methanol
  6. customAfter evaporation of the volatiles

Sources & evidence

ORD record
ord-2cf62ee122fb4ad5809d9a0c6a898dd5
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

Loading…