Hydrochloric Acid → 2-{2-[5(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro [1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid

HRID 1046942Notes

Reaction equation

HRID 1046942 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[N:22]([C:23](=[O:33])[C:24]2[C:29]([F:30])=[CH:28][C:27]([F:31])=[CH:26][C:25]=2[F:32])[N:21]=[C:20]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[S:19]1)=[O:4].[Li+].[OH-].Cl>C1COCC1.CO.O>[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:20]2[S:19][CH:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][CH2:10][C:6]3[O:7][CH:8]=[CH:9][C:5]=3[C:3]([OH:4])=[O:2])[N:22]([C:23](=[O:33])[C:24]3[C:29]([F:30])=[CH:28][C:27]([F:31])=[CH:26][C:25]=3[F:32])[N:21]=2)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 672793392-{2-[5(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid methyl ester

Product 1

HCID 580256232-{2-[5(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro [1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 2-{2-[5(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid methyl ester (0.49 mmol) in THF/MeOH/H2O (3:2:1), is added LiOH (3 N) (4.9 mmol). After stirring for 12 hours, the reaction is acidified with HCl (1 N) and extracted with ethyl acetate. The organic layer is dried over MgSO4, filtered, and concentrated. The residue is purified using preparative LC/MS to give 2-{2-[5(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-furan-3-carboxylic acid as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.26-7.23 (m, 3H), 7.20 (d, J=1.9, 1H), 7.10-7.05 (m, 1H), 7.03-6.99 (m, 1H), 6.86 (d, J=8.1, 1H), 6.78-6.74 (m, 3H), 6.55 (d, J=1.9, 1H), 6.55-6.50 (m, 2H), 5.38-5.21 (m, 2H); LC/MS (ES+): 557.1 (M+1)+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified

Sources & evidence

ORD record
ord-b864df30adb24acbaab817d888c2365d
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

Loading…