Methanol → HCID 18400197, compound

HRID 726545Notes

Reaction equation

HRID 726545 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].CO.[OH-].[Na+]>C1COCC1.[OH-].[Na+]>[NH2:19][S:16]([C:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[S:6][C:7]=2[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=[O:17])=[O:18]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15340372HCID 15340372, compound

Product 1

HCID 18400197HCID 18400197, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-(4-(aminosulfonyl)phenyl)-5-(4-fluorophenyl)thiophene-2-carboxylic acid methyl ester (Example 1, Step 5) (0.210 g) in THF (2.0 mL) were added MeOH (1.0 mL), NaOH 1N (1.0 mL) and a few drops of NaOH 10N. The resulting mixture was heated at 45° C. for 2 h and the reaction was then partitioned between EtOAc and HCl (3N) to provide the title product as a white solid (0.200 g). 1H NMR (CD3COCD3) δ6.60 (2H, s), 7.15 (2H, t), 7.35 (2H, q), 7.45 (2H, d), 7.82 (2H, d), 7.87 (1H, s).

Workup

  1. customthe reaction was then partitioned between EtOAc and HCl (3N)

Sources & evidence

ORD record
ord-7305150849c34073a12717eb5584545c
Source dataset
uspto-grants-1998_01
Patent number
US05710140

Reaction notes

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