Water → 3-[(2-Acetylamino-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid

HRID 1807979Notes

Reaction equation

HRID 1807979 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:14]([CH:16]1[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH:17]1[NH:23][C:24](=[O:26])[CH3:25])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:4].O.[Li+].[OH-]>O1CCOCC1>[C:24]([NH:23][CH:17]1[CH2:18][CH:19]([CH3:22])[CH2:20][CH2:21][CH:16]1[C:14]([N:10]([CH:11]([CH3:13])[CH3:12])[C:9]1[CH:8]=[C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])=[O:15])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 597523653-[(2-Acetylamino-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 100490073-[(2-Acetylamino-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[(2-Acetylamino-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (8.5 mg, 0.019 mmol) was dissolved in a 4:1 mixture of dioxane:H2O (250 ul) and then LiOH 1N (22 ul, 0.023 mmol) was added. After 22 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 to give 7.5 mg (91%) of 3-[(2-Acetylamino-4-methyl-cyclohexanecarbonyl)-isopropyl-amino]-5-phenyl-thiophene-2-carboxylic acid (Compound 12).

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

Sources & evidence

ORD record
ord-c738764a7830494287cde6898ea18954
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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