Trifluoroacetic acid → HCID 67236013, compound

HRID 1505338Notes

Reaction equation

HRID 1505338 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=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)[CH3:9]>ClCCl>[CH2:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=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)[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322477HCID 68322477, compound2×

Product 1

HCID 67236013HCID 67236013, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask 1,1-dimethylethyl [(1R)-2-({6-[(2-ethylphenyl)oxy]-3-pyridinyl}amino)-1-methyl-2-oxoethyl]carbamate (Intermediate 47, 251.1 mg) was dissolved in dichloromethane (2 mL) to give a pale orange solution. Trifluoroacetic acid (2 mL, 26.0 mmol) was added. The reaction mixture was stirred at room temperature. After 20 minutes the solvent was evaporated under vacuum affording a yellow oil which was charged on a 5 g SCX cartridge and 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 (170.0 mg).

Workup

  1. customto give a pale orange solution
  2. customAfter 20 minutes the solvent was evaporated under vacuum
  3. customaffording a yellow oil which
  4. additionwas charged on a 5 g SCX cartridge
  5. customflushed with 25 mL of MeOH
  6. customThe ammonia eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-ebecfece4b0744c19357420a39d65ea0
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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