Lithium hydroxide, monohydrate → 3-(2-Carboxy-1-cyclohexyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 579194Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 3-(1-cyclohexyl-2-ethoxycarbonyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (300 mg, 0.72 mmol, 1.0 equiv) in THF (2.0 mL), EtOH (1.0 mL) and water (2.0 mL) was added LiOH.H2O (152 mg, 3.6 mmol, 5.0 equiv). The mixture was stirred at 55° C. for 20 minutes. The organic solvent was then evaporated. To the resulting solution was added 3.0 N HCl aq. solution until pH=5˜6. The solid was then collected by filtration and washed with water. The filtrate was extracted with EtOAc and the organic layer was washed with sat. NaHCO3 aq. solution, brine, dried over Na2SO4, and concentrated in vacuo. The crude material was continued to the next step with no further purification.

Workup

customThe organic solvent was then evaporated
additionTo the resulting solution was added 3.0 N HCl aq. solution until pH=5˜6
filtrationThe solid was then collected by filtration
washwashed with water
extractionThe filtrate was extracted with EtOAc
washthe organic layer was washed with sat. NaHCO3 aq. solution, brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was continued to the next step with no further purification

Sources & evidence

ORD record: ord-db5eb5b91acf4718aa92668458aa9664
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040690B2

Reaction notes

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