Lithium Hydroxide → 3-(2-Hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-yl)-acrylic acid

HRID 1872244Notes

Reaction equation

HRID 1872244 reaction equation
C([O:3][C:4](=[O:29])[CH:5]=[CH:6][CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:8]1[C:25](=[O:28])[NH:26][OH:27])C.[OH-].[Li+]>C1COCC1.O>[OH:27][NH:26][C:25]([CH:8]1[CH:7]([CH:6]=[CH:5][C:4]([OH:29])=[O:3])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:14]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)(=[O:16])=[O:15])=[O:28]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 541788313-(2-Hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-yl)-acrylic acid ethyl ester

Product 1

HCID 545133623-(2-Hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-yl)-acrylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-Hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-yl)-acrylic acid ethyl ester (41 mg, 0.096 mmoL) in 0.96 mL THF and 1.1 mL water was added lithium hydroxide (12 mg, 0.288 mmoL) at ambient temperature. After 3.5 hours the reaction solvent was evaporated under reduced pressure, and the residue was diluted with water and washed twice with diethyl ether. The water layer was acidified to pH=1 and extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The residue was freeze dried to yield 3-(2-Hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-azepan-3-yl)-acrylic acid; MS: (M+H)+ =399, (M+NH4)+ =416, (M-H)- =397.

Workup

  1. customAfter 3.5 hours the reaction solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. washwashed twice with diethyl ether
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customdried

Sources & evidence

ORD record
ord-00e89e1656684f719bab4eff8f9927fe
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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