Water → HCID 178461275, compound

HRID 749358Notes

Reaction equation

HRID 749358 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[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].O.[Li+].[OH-]>O1CCOCC1>[OH:26][C@H:23]1[CH2:24][CH2:25][C@H:20]([N:10]([C:11]([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]2)=[O:12])[C:9]2[CH:8]=[C:7]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178499282HCID 178499282, compound

Product 1

HCID 178461275HCID 178461275, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[(trans-4-Hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (34 mg, 0.075 mmol) was dissolved in a 4:1 mixture of dioxane:H2O (1 ml) and then LiOH 1N (375 ul, 0.375 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 21 mg (64%) of 3-[(trans-4-Hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid (Compound 15).

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-497d0495c3854c63b502ba9bf35f4090
Source dataset
uspto-grants-2008_07
Patent number
US07402608B2

Reaction notes

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