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

HRID 579194
Notes
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Reaction equation

HRID 579194 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 666841133-(1-Cyclohexyl-2-ethoxycarbonyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 666846033-(2-Carboxy-1-cyclohexyl-ethylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent

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

  1. customThe organic solvent was then evaporated
  2. additionTo the resulting solution was added 3.0 N HCl aq. solution until pH=5˜6
  3. filtrationThe solid was then collected by filtration
  4. washwashed with water
  5. extractionThe filtrate was extracted with EtOAc
  6. washthe organic layer was washed with sat. NaHCO3 aq. solution, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes