Trifluoroacetic acid → 2-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]butanoic acid

HRID 56653Notes

Reaction equation

HRID 56653 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]#[N:26])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH2:22][CH3:23])[C:15]([O:17]C(C)(C)C)=[O:16])[C:10](=[O:24])[CH:9]=2)[CH:7]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]#[N:26])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]([CH:14]([CH2:22][CH3:23])[C:15]([OH:17])=[O:16])[C:10](=[O:24])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117622863tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]butanoate

Product 1

HCID 1176227462-[4-(5-Chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]butanoic acid

Procedure

543 mg (purity 59%, 0.86 mmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]butanoate (racemate) were hydrolysed with 20 eq. of TFA according to General Method 6A. Yield: 425 mg (purity 60%, 94% of theory)

Sources & evidence

ORD record
ord-135080ae1302460e9ccce345fe5ef5ea
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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