Lithium Hydroxide → 3-(4-Carboxy-1-cyclohexyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 579191Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[O:4].[OH-].[Li+]>C1COCC1.CCO.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-(1-Cyclohexyl-4-ethoxycarbonyl-butylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (40 mg, 0.09 mmol, 1.0 equiv) in THF (0.4 mL), EtOH (0.2 mL), water (0.4 mL) was added lithium hydroxide (18.9 mg, 0.45 mmol, 5.0 equiv). The resulting mixture was stirred at 50° C. for 2 hours, after which the organic solvent was removed under vacuum. The resulted solution was neutralized by addition of 1.0 N HCl aq. solution until pH=6. The mixture was extracted with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to product 30 mg (yield 83%).

Workup

customafter which the organic solvent was removed under vacuum
additionThe resulted solution was neutralized by addition of 1.0 N HCl aq. solution until pH=6
extractionThe mixture was extracted with EtOAc
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-f80c70fd80ba433db8bf6df61b4e3352
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040690B2

Reaction notes

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