Lithium hydroxide, monohydrate → [(4-Chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid

HRID 2079605

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of [(4-chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid methyl ester (1.03 g, 2.7 mmol) in THF (20 mL) was added an aqueous solution (10 mL) of lithium hydroxide monohydrate (168 mg, 4.0 mmol) slowly under ice-cooled condition. The reaction mixture was stirred for 2 h at 25° C. THF was evaporated in vacuo and water was added. The mixture was washed with diethyl ether. The aqueous layer was acidified with 1(N) hydrochloride acid to pH 6, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water, dried (Na2SO4), and evaporated under reduced pressure to yield the title compound as pure solid compound, which used as such in the final coupling reaction. Yield: 810 mg (84%).

Workup

temperaturecooled condition
customTHF was evaporated in vacuo and water
additionwas added
washThe mixture was washed with diethyl ether
extractionextracted with ethyl acetate (3×20 mL)
washThe combined organic layers were washed with water
dry with materialdried (Na2SO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-512a9d46513b489095e7cb4249b6e0e3
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932269B2

Linked notes

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