Lithium hydroxide, monohydrate → HCID 22496193, compound

HRID 2193940Notes

Reaction equation

HRID 2193940 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[C:8]([NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])[C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:4].O[Li].O>C1COCC1.CO.O>[CH:10]([C:9]1[C:8]([NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])=[C:7]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67299074HCID 67299074, compound

Product 1

HCID 22496193HCID 22496193, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

3-Isopropyl-[(4-methyl-cyclohexanecarbonyl)-amino]-5-m-tolyl-thiophene-2-carboxylic acid methyl ester (30 mg, 0.073 mmol) was taken in a mixture of THF:MeOH:H2O (3:2:1, 3 mL) and then added 1N aqueous solution of LiOH.H2O (0.44 mL, 0.438 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 preparative TLC using chloroform:methanol:acetic acid (9:1:0.1) to obtain 3-Isopropyl-[(4-methyl-cyclohexanecarbonyl)-amino]-5-m-tolyl-thiophene-2-carboxylic acid (15 mg, 52%) as a white solid. 1H NMR (CDCl3, 400 MHz): (s, 2H), 7.38 (t, 1H), 7.24 (m, 1H), 7.08 (s, 1H), 5.01 (s, 1H), 2.42 (s, 3H), 2.10-0.62 (m, 20H). ESI− (M-H): 398.

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 preparative TLC

Sources & evidence

ORD record
ord-b2dbcce169bd4ff08517eb1e2ab594f8
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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