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 1694361Notes

Reaction equation

HRID 1694361 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-f39cbff6a1b04dd89280b2618ac875ab
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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