Methanol → {2-[5-(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetic acid

HRID 1046937Notes

Reaction equation

HRID 1046937 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[N:16]([C:17](=[O:27])[C:18]2[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=2[F:26])[N:15]=[C:14]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[S:13]1.C1COCC1.CO.[Li+].[OH-]>C(OCC)(=O)C.O>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:14]2[S:13][CH:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[O:5][CH2:4][C:3]([OH:35])=[O:2])[N:16]([C:17](=[O:27])[C:18]3[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=3[F:26])[N:15]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67278830{2-[5-(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetic acid methyl ester

Product 1

HCID 67278887{2-[5-(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {2-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetic acid methyl ester (2.93 mmol) in 30 mL of a mixture of THF and MeOH (3:2), is added LiOH (1 M) (30 mL). After stirring for 12 hours the reaction is complete as determined by LC/MS. The reaction is diluted with ethyl acetate and water, washed with brine and dried over MgSO4 and the solvent is removed from the reaction mixture to yield {2-[5-(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxy}-acetic acid: 1H NMR (400 MHz, acetone-d6) δ 7.66 (m, 3H), 7.39 (m, 1H), 7.3 (dd, J1=7.6 Hz, J2=1.6 Hz, 1H), 7.22 (m, 4H), 7.13 (m, 1H), 7.07 (t, J=7.6 Hz, 1H), 4.94 (s, 2H); LC/MS (ES+): 491.0 (M+1)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customthe solvent is removed from the reaction mixture

Sources & evidence

ORD record
ord-2a22f831ca7647f6bd631c1753448366
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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