Trifluoroacetic acid → HCID 90203539, compound

HRID 1480273Notes

Reaction equation

HRID 1480273 reaction equation
[CH:1]1([C:4]2[C:5]([O:25][C@@H:26]([CH3:31])[C:27]([F:30])([F:29])[F:28])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[C:5]([O:25][C@@H:26]([CH3:31])[C:27]([F:30])([F:28])[F:29])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:14]([OH:16])=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90214929tert-butyl 2-[[5-cyclopropyl-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoate

Product 1

HCID 90203539HCID 90203539, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-[[5-cyclopropyl-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoate (example 199a, 0.485 g, 1.09 mmol) in dichloromethane (3 ml) was added trifluoroacetic acid (3.73 g, 2.52 ml, 32.8 mmol) and the reaction mixture was stirred at room temperature for 14 hours. Volatiles were removed in vacuo and the residue was dissolved in toluene followed by evaporation to dryness. The procedure was repeated twice to yield the title compound (446 mg) as a crude solid which was used without any purification. MS (ESI, m/z): 387.5 (M−H+).

Workup

  1. customVolatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in toluene
  3. customfollowed by evaporation to dryness

Sources & evidence

ORD record
ord-1c9d3879c3994f23a3ee7c7ba490eb15
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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