Water → HCID 178454408, compound

HRID 2099626Notes

Reaction equation

HRID 2099626 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=2)=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[Li+].[OH-].O>C1COCC1.O.CO>[C:31]1([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([CH:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])[CH2:24][CH2:25]3)[C:11]([C@H:13]3[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]3)=[O:12])[CH:8]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178499275HCID 178499275, compound

Product 1

HCID 178454408HCID 178454408, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 5-cyclohex-1-enyl-3-[(1-isobutyryl-piperidin-4-yl)-(trans-4-methyl cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (50 mg, 0.10 mmol) in THF:H2O:MeOH (3:1:2) (3 mL), was added LiOH in water (1N) (0.3 mL, 0.3 mmol). The reaction mixture was stirred at 70° C. for 5 h. The mixture was concentrated under reduced pressure on a rotary evaporator and the residue was treated with a solution of 0.1 N HCl and extracted in EtOAc. The EtOAc layer was dried over Na2SO4. Filtration and removal of the solvent under reduced pressure on a rotary evaporator followed by HPLC purification afforded 5-cyclohex-1-enyl-3-[(1-isobutyryl-piperidin-4-yl)-(trans-4-methyl cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (30.0 mg, 61%) as a foam.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure on a rotary evaporator
  2. additionthe residue was treated with a solution of 0.1 N HCl
  3. extractionextracted in EtOAc
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationFiltration and removal of the solvent under reduced pressure
  6. customon a rotary evaporator
  7. customfollowed by HPLC purification

Sources & evidence

ORD record
ord-31a6d9a0d7bf4c078e3a0708037ce269
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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