Trifluoroacetic acid → HCID 90203469, compound

HRID 1480259Notes

Reaction equation

HRID 1480259 reaction equation
[CH:1]1([CH2:4][C:5]([NH:14][C:15]([C:17]2[CH:22]=[C:21]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:20]([CH:29]3[CH2:31][CH2:30]3)=[CH:19][N:18]=2)=[O:16])([CH3:13])[C:6]([O:8]C(C)(C)C)=[O:7])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[CH:1]1([CH2:4][C:5]([NH:14][C:15]([C:17]2[CH:22]=[C:21]([O:23][CH2:24][C:25]([F:26])([F:27])[F:28])[C:20]([CH:29]3[CH2:31][CH2:30]3)=[CH:19][N:18]=2)=[O:16])([CH3:13])[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90203565HCID 90203565, compound

Product 1

HCID 90203469HCID 90203469, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-cyclopropyl-2-[[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonyl]amino]-2-methyl-propanoate (example 186c, 103 mg, 233 μmol) in dichloromethane (0.5 ml) was added TFA (159 mg, 108 μl, 1.4 mmol). The reaction mixture was stirred at room temperature for 14 hours. Volatiles were removed in vacuo and the residue was dissolved in a mixture of dichlormethane and toluene followed by evaporation to dryness. The procedure was repeated twice until a precipitate formed. The precipitate was dried under high vacuum to yield the title compound (95 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 a mixture of dichlormethane and toluene
  3. customfollowed by evaporation to dryness
  4. customformed
  5. customThe precipitate was dried under high vacuum

Sources & evidence

ORD record
ord-1eb7f0cd2acb44efa57fb63bae4a1fe2
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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