Lithium hydroxide, monohydrate → HCID 59267858, compound

HRID 553588Notes

Reaction equation

HRID 553588 reaction equation
C([O:3][C:4](=[O:20])[C:5]([S:8]([C:11]1[CH:19]=[CH:18][C:14]2[N:15]=[CH:16][S:17][C:13]=2[CH:12]=1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.O.[OH-].[Li+]>O1CCOCC1.O>[S:17]1[C:13]2[CH:12]=[C:11]([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:20])=[O:3])(=[O:10])=[O:9])[CH:19]=[CH:18][C:14]=2[N:15]=[CH:16]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59267946HCID 59267946, compound

Product 1

HCID 59267858HCID 59267858, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 778 mg (2.48 mmol) of 2-(benzothiazole-6-sulfonyl)-2-methyl-propionic acid ethyl ester in THF/water (1/1, 24 mL) are added 208 mg (4.97 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 5 h. The organic solvent is removed under reduced pressure. The basic aqueous layer is washed with diethyl ether (10 mL), then cooled in an ice bath and acidified with 6M aqueous HCl solution to pH 2. The acidic aqueous layer is extracted with ethyl acetate (3×15 mL). The combined organic extracts are dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 686 mg of 2-(benzothiazole-6-sulfonyl)-2-methyl-propionic acid as a pale yellow solid. Yield: 66%; ES-MS: m/z 569 [2M−H]; 1H NMR (250 MHz, DMSO-d6) δ ppm 1.51 (6H, s), 7.91 (1H, dd, J=8.68, 1.98 Hz), 8.30 (1H, d, J=8.68 Hz), 8.79 (1H, d, J=1.83 Hz), 9.70 (1H, s);

Workup

  1. customThe organic solvent is removed under reduced pressure
  2. washThe basic aqueous layer is washed with diethyl ether (10 mL)
  3. temperaturecooled in an ice bath
  4. extractionThe acidic aqueous layer is extracted with ethyl acetate (3×15 mL)
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e8e278c48a3542c298741e695ad9081d
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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