Trifluoroacetic acid → HCID 67235318, compound

HRID 1023536Notes

Reaction equation

HRID 1023536 reaction equation
FC(F)(F)C(O)=O.CC([N:12]([C@H:16]([CH3:35])[C:17]([NH:19][C:20]1[CH:21]=[N:22][C:23]([O:26][C:27]2[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:34])=[CH:24][CH:25]=1)=[O:18])C(=O)[O-])(C)C>ClCCl>[CH3:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:34])[C:27]=1[O:26][C:23]1[N:22]=[CH:21][C:20]([NH:19][C:17](=[O:18])[C@@H:16]([CH3:35])[NH2:12])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673586HCID 86673586, compound2×

Product 1

HCID 67235318HCID 67235318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask 1,1-dimethylethyl[(1R)-2-({6-[(2,6-dimethylphenyl)oxy]-3-pyridinyl}amino)-1-methyl-2-oxoethyl]carbamate (Intermediate 43, 282 mg) was dissolved in dichloromethane (2 mL) to give a yellow solution. Trifluoroacetic acid (2 mL, 26.0 mmol) was added. The reaction mixture was stirred at room temperature. After 20 min, the solvent was evaporated under vacuum affording a yellow oil that was charged on a 5 g SCX cartridge. It was then flushed with 25 mL of MeOH followed by 25 mL of 2M solution of ammonia in MeOH. The ammonia eluate was evaporated under vacuum to afford the title compound as a yellow oil which solidified (173.8 mg).

Workup

  1. customto give a yellow solution
  2. customthe solvent was evaporated under vacuum
  3. customaffording a yellow oil that
  4. additionwas charged on a 5 g SCX cartridge
  5. customIt was then flushed with 25 mL of MeOH
  6. customThe ammonia eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-1fcd8d150d784bd7ab2cbe8311fd2c90
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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