Trifluoroacetic acid → HCID 90203975, compound

HRID 1480266Notes

Reaction equation

HRID 1480266 reaction equation
[CH:1]1([C:4]2[C:5]([O:25][CH2:26][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][CH2:26][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 90204432Tert-butyl 2-[[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoate

Product 1

HCID 90203975HCID 90203975, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-[[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoate (example 194a, 0.47 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 (432 mg) as a crude solid which was used without any purification. MS (ESI, m/z): 373.5 (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-43b08f77a50b4e968bb0ab341a883a65
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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