Lithium hydroxide, monohydrate → HCID 67298923, compound

HRID 2193911Notes

Reaction equation

HRID 2193911 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:8][C:9]=1[N:10]([CH:23]([C:30]1[O:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[S:11]([C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([Cl:21])=[CH:16][C:15]=1[CH3:22])(=[O:13])=[O:12])=[O:4].O[Li].O>C1COCC1.CO.O>[O:34]1[C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[CH:31]=[C:30]1[CH:23]([N:10]([S:11]([C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([Cl:21])=[CH:16][C:15]=1[CH3:22])(=[O:12])=[O:13])[C:9]1[CH:8]=[C:7]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67299252HCID 67299252, compound

Product 1

HCID 67298923HCID 67298923, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3-[(3-Benzofuran-2-yl-benzyl)-(4-chloro-2,5-dimethyl-benzenesulfonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (20 mg, 0.031 mmol) was taken in a mixture of THF:MeOH:H2O (3:2:1, 3 mL) and then added 1N aqueous solution of LiOH.H2O (0.20 mL, 0.186 mmol). The reaction mixture was stirred at room temperature for 12 h. Solvents were removed and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified using 10% KHSO4 solution. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using dichloromethane and methanol (9:1) to obtain 3-[(3-Benzofuran-2-yl-benzyl)-(4-chloro-2,5-dimethyl-benzene-sulfonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid (14 mg, 70%) as a white solid. 1H NMR (DMSO, 400 MHz): δ7.93 (s, 1H), 7.84 (s, 1H), 7.74 (bd, 1H), 7.65-7.22 (m, 14H), 4.95 (s, 2H), 2.33, 2.23 (2s, 6H).

Workup

  1. customSolvents were removed
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cbb1657b9010448c92a99018e942d12e
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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