Trifluoroacetic acid → HCID 67235318, compound

HRID 1505335Notes

Reaction equation

HRID 1505335 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[O:16][C:17]1[N:22]=[CH:21][C:20]([NH:23][C:24](=[O:35])[C@H:25]([NH:27]C(=O)OC(C)(C)C)[CH3:26])=[CH:19][CH:18]=1>ClCCl>[CH3:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH3:8])[C:10]=1[O:16][C:17]1[N:22]=[CH:21][C:20]([NH:23][C:24](=[O:35])[C@@H:25]([CH3:26])[NH2:27])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322497HCID 68322497, 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-bb2bcbfee465492daf13317d26cdb656
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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