Water → HCID 178501192, compound

HRID 1190007Notes

Reaction equation

HRID 1190007 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([O:26][CH2:27][O:28][CH3:29])[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:30]1([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([C@H:20]3[CH2:21][CH2:22][C@H:23]([O:26][CH2:27][O:28][CH3:29])[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)[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178501191HCID 178501191, compound

Product 1

HCID 178501192HCID 178501192, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-cyclohex-1-enyl-3-[(trans-4-methoxymethoxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (775 mg, 1.54 mmol) in THF: H2O: MeOH (3:1:2) (10 mL), was added LiOH in water (1N) (4.6 mL, 4.6 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-[(trans-4-methoxymethoxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (380 mg, 50%) 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-d88ebf7aedb54ea79502519b843718c0
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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