Sodium Hydroxide → HCID 56967004, compound

HRID 1036915Notes

Reaction equation

HRID 1036915 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:30]([O:32]CC)=[O:31])[CH:24]=2)[NH:19]1)(=[O:10])=[O:9].O.[OH-].[Li+].[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[CH2:27][C:26]([CH3:28])([CH3:29])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:30]([OH:32])=[O:31])[CH:24]=2)[NH:19]1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 67291815HCID 67291815, compound

Product 1

HCID 56967004HCID 56967004, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of ethyl 2-(2-(2-fluorophenylsulfonamido)phenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (crude 0.62 mmol) in ethanol was added a solution of lithium hydroxide monohydrate (129 mg, 3.08 mmol) and sodium hydroxide (50 mg, 1.23 mmol) in water (1.5 mL) at room temperature. The reaction mixture was stirred at 85° C. overnight. The reaction mixture was concentrated in vacuo. The residue was diluted with water, adjusted pH=3˜4 by 1M aqueous hydrochloric acid, extracted with ethyl acetate. The combined organic layer was washed by brine, dried over anhydrous Sodium sulfate, concentrated in vacuo. The residue was purified by HPLC to give 2-[2-(2-fluoro-benzenesulfonylamino)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid LC/MS m/e obsd. (ESI+) [(M+H)+] 455.20.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed by brine
  5. dry with materialdried over anhydrous Sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-66429a651458402a8da414bdfc7191f5
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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