Methanol → HCID 67279321, compound

HRID 1694353Notes

Reaction equation

HRID 1694353 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]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]=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[S:13]2)[C:7]=1[O:35][CH3:36].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:8]3[C:7]([O:35][CH3:36])=[C:6]([CH:11]=[CH:10][CH:9]=3)[O:5][CH2:4][C:3]([OH:37])=[O:2])[N:16]([C:17](=[O:27])[C:18]3[C:19]([F:26])=[CH:20][C:21]([F:25])=[CH:22][C:23]=3[F:24])[N:15]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67279598HCID 67279598, compound

Product 1

HCID 67279321HCID 67279321, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-acetic acid methyl ester (2.47 mmol) in 30 mL of a mixture of THF and MeOH (3:2), is added LiOH (1 M) (25 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 {3-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-acetic acid: LC/MS (ES+): 521.1 (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-1533bbfc1b74485da60ee03625477faf
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

Loading…