Water → VCH-759

HRID 1807987Notes

Reaction equation

HRID 1807987 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:8][C:9]=1[N:10]([C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([CH3:37])[CH2:33][CH2:32]1)=[O:30])[CH:11]1[CH2:16][CH2:15][CH:14]([O:17]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:13][CH2:12]1)=[O:4].O.[Li+].[OH-]>O1CCOCC1>[OH:17][CH:14]1[CH2:15][CH2:16][CH:11]([N:10]([C:29]([CH:31]2[CH2:32][CH2:33][CH:34]([CH3:37])[CH2:35][CH2:36]2)=[O:30])[C:9]2[CH:8]=[C:7]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 597523093-{(4-Methyl-cyclohexanecarbonyl)-[4-(4-nitro-benzoyloxy)-cyclohexyl]-amino}-5-phenyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 10455984VCH-759Yield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-{(4-Methyl-cyclohexanecarbonyl)-[4-(4-nitro-benzoyloxy)-cyclohexyl]-amino}-5-phenyl-thiophene-2-carboxylic acid methyl ester (44 mg, 0.073 mmol) was dissolved in a 4:1 mixture of dioxane:H2O (1 ml) and then LiOH 1N (365 ul, 0.365 mmol) was added. After 4 hours of stirring at room temperature, solvents were removed and then partitioned between 5 ml of H2O acidified to pH 4 and 5 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×5 mL). The combined ethyl acetate layer was dried (Na2SO4) and concentrated. The residue was purified by preparative chromatography (10% MeOH/CH2Cl2) to obtain 15 mg (47%) of 3-[(4-Hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid.

Workup

  1. customsolvents were removed
  2. custompartitioned between 5 ml of H2O
  3. customThe organic layer was separated
  4. washthe aqueous phase was washed twice with ethyl acetate (2×5 mL)
  5. dry with materialThe combined ethyl acetate layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by preparative chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-dc6ba8f0756445418d180830db67c4f6
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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