Trifluoroacetic acid → HCID 67236013, compound

HRID 1023539Notes

Reaction equation

HRID 1023539 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[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][CH3:34])=[CH:24][CH:25]=1)=[O:18])C(=O)[O-])(C)C>ClCCl>[CH2:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][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)[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673587HCID 86673587, 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-00ab6c3a5bc94df6b8c5f7ab9f1d8bd5
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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