Trifluoroacetic acid → HCID 67235885, compound

HRID 1505341Notes

Reaction equation

HRID 1505341 reaction equation
[CH3:1][C@@H:2]([NH:22]C(=O)OC(C)(C)C)[C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([O:20][CH3:21])[CH:14]=2)=[CH:10][CH:11]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[N:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[C@@H:2]([CH3:1])[NH2:22])=[CH:11][CH:10]=2)=[CH:14][C:15]=1[O:20][CH3:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 710067841,1-dimethylethyl {(1R)-1-methyl-2-[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]-2-oxoethyl}carbamate2×

Product 1

HCID 67235885HCID 67235885, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {(1R)-1-methyl-2-[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]-2-oxoethyl}carbamate (Intermediate 51, 350 mg) in dry dichloromethane (7.5 mL), TFA (2.5 mL, 32.4 mmol) was slowly added and the reaction mixture was stirred for 1.5 hours at room temperature. The solvent and the excess of TFA were evaporated and the residue was purified with an SCX cartridge (10 g) to afford the title compound as a colourless oil (258 mg).

Workup

  1. customThe solvent and the excess of TFA were evaporated
  2. customthe residue was purified with an SCX cartridge (10 g)

Sources & evidence

ORD record
ord-20e3c46e54714a2eb530123888ffbbbd
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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