Trifluoroacetic acid → HCID 18617634, compound

HRID 1264242Notes

Reaction equation

HRID 1264242 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)=[CH:10]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.O>[C:6]([CH2:8][N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=2)=[CH:10]1)([OH:7])=[O:5]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18617601HCID 18617601, compound

Product 1

HCID 18617634HCID 18617634, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-(1-tert-butoxycarbonylmethyl-6-oxo-1,6-dihydropyridin-3-yl)benzoate [1.03 g, 2.88 mmol, reference example 85b] in CH2Cl2 [10 ml] and H2O [0.125 ml] is added trifluoroacetic acid [2.5 ml]. After 18 hours removed solvent in vacuo and triturated the resulting solid with methylene chloride to give 0.815 g of the product as a white solid in 93.9% yield. 1H NMR (1:1 CD3OD:CDCl3): δ 1.43 (3H, t, J=7 Hz), 4.40 (2H, q, J=7 Hz), 4.81 (2H, s), 6.73 (1H, d, J=9 Hz), 7.60 (2H, d, J=8 Hz), 7.60 (1H, s), 7.88 (1H, d, J=9.0 Hz), 8.09 (2H, d, J=8 Hz). MS (ion spray) m/z 302 (M+H)+.

Workup

  1. customAfter 18 hours removed solvent in vacuo
  2. customtriturated the resulting solid with methylene chloride

Sources & evidence

ORD record
ord-50d0ec5f3831414c88fe448a6f77ec6e
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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