Lithium hydroxide, monohydrate → HCID 67298923, compound

HRID 1015627Notes

Reaction equation

HRID 1015627 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-08616466212e477d921515dc70594810
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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