Lithium hydroxide, monohydrate → HCID 10189576, compound

HRID 2193909Notes

Reaction equation

HRID 2193909 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:8][C:9]=1[N:10]([S:19]([C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Cl:29])=[CH:24][C:23]=1[CH3:30])(=[O:21])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[CH:13]=1)=[O:4].O[Li].O>C1COCC1.CO.O>[Cl:29][C:25]1[C:26]([CH3:28])=[CH:27][C:22]([S:19]([N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[CH:13]=2)[C:9]2[CH:8]=[C:7]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])(=[O:20])=[O:21])=[C:23]([CH3:30])[CH:24]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 20775758HCID 20775758, compound

Product 1

HCID 10189576HCID 10189576, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3-[(4-Chloro-2,5-dimethyl-benzenesulfonyl)-(3-iodo-benzyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (25 mg, 0.038 mmol) was taken in a mixture of THF:MeOH:H2O (3:2:1, 3 mL) and then added 1N aqueous solution of LiOH.H2O (0.24 mL, 0.228 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-[(4-Chloro-2,5-dimethyl-benzene-sulfonyl)-(3-iodo-benzyl)-amino]-5-phenyl-thiophene-2-carboxylic acid (22 mg, 88%) as a white solid. 1H NMR (CDCl3, 400 MHz): 7.69 (m, 3H), 7.57 (m, 3H), 7.42 (m, 3H), 7.33 (d, 1H), 7.16 (s, 1H), 6.04 (dd, 1H), 4.90 (bs, 2H), 2.36 (s, 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-0041772d90df45b389100ab811d6e919
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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