Potassium Carbonate → (3S)-4,4,4-trifluoro-3-(2-{[4-(4-fluorophenyl)-2-oxo-2H-chromen-7-yl]thio}-1,3-thiazol-5-yl)-3-hydroxybutanoic acid

HRID 2116644Notes

Reaction equation

HRID 2116644 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[F:20][C:21]([F:35])([F:34])[C@:22]([OH:33])([C:27]1[S:31][C:30]([SH:32])=[N:29][CH:28]=1)[CH2:23][C:24]([OH:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[F:35][C:21]([F:20])([F:34])[C@@:22]([C:27]1[S:31][C:30]([S:32][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)=[CH:7][C:8](=[O:12])[O:9]3)=[CH:4][CH:3]=2)=[N:29][CH:28]=1)([OH:33])[CH2:23][C:24]([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233702437-Bromo-4-(4-fluorophenyl)-chromen-2-oneHCID 178525608HCID 178525608, compound

Product 1

HCID 59814846(3S)-4,4,4-trifluoro-3-(2-{[4-(4-fluorophenyl)-2-oxo-2H-chromen-7-yl]thio}-1,3-thiazol-5-yl)-3-hydroxybutanoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Employing the procedure of Example 1, Step 3, using 7-bromo-4-(4-fluorophenyl)-2H-chromen-2-one (0.467 g, 1.5 mmol), (3S)-4,4,4-trifluoro-3-hydroxy-3-(2-mercapto-1,3-thiazol-5-yl)butanoic acid (enantiomer #1, 0.400 g, 1.5 mmol) and potassium carbonate (0.708 g, 5.1 mmol) in NMP at 120° C., the title compound was obtained. Purification was done on silica gel (CH2Cl2/MeOH/HOAc; 90:10:0.5). [α]25D−30° (c=0.5, CHCl3). 1H NMR (400 MHz, acetone-d6): δ 7.99 (s, 1H), 7.68 (m, 2H), 7.58 (m, 2H), 7.48 (dd, 1H), 7.39 (dd, 2H), 6.43 (s, 1H), 3.33 (dd, 2H).

Workup

  1. customat 120° C.

Sources & evidence

ORD record
ord-2fa7bd10c6204a0fb45dfe9cd7d89857
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

Loading…