Sodium Hydroxide → HCID 71203616, compound

HRID 1844554Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([C:19]2[S:23][C:22]([C:24]([O:26]C)=[O:25])=[C:21]([CH3:28])[C:20]=2[CH3:29])=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([C:19]2[S:23][C:22]([C:24]([OH:26])=[O:25])=[C:21]([CH3:28])[C:20]=2[CH3:29])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-3,4-dimethylthiophene-2-carboxylate (step-5, 0.2 g, 0.45 mmol) was suspended in ethanol (10 ml). Aqueous solution of NaOH (0.09 g. 2.24 mmol in water 2 ml) was added to the reaction mixture at 0° C. The reaction mixture was heated at 80° C. under stirring for 1.5 hour. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. Dilute hydrochloric acid was added to the separated aqueous layer to bring the pH of the solution to between 6 and 7. The resulting mixture was extracted with ethyl acetate (2×25 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain the title compound 9f (0.17 g, 86.0%).

Workup

concentrationThe reaction mixture was then concentrated under reduced pressure
additionDilute hydrochloric acid was added to the separated aqueous layer
extractionThe resulting mixture was extracted with ethyl acetate (2×25 ml)
dry with materialThe combined organic layer was dried over anhydrous Na2SO4
customThe solvent was evaporated from the dried organic layer under reduced pressure

Sources & evidence

ORD record: ord-4e075b51bce34a92836d0224ea3c668e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946432B2

Reaction notes

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