Sodium Hydroxide → 4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoic acid

HRID 412457Notes

Reaction equation

HRID 412457 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[C:27]([O:26][C:24]([N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=1)[C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 697341314-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoic acid methyl ester

Product 1

HCID 223111164-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-{[tert-Butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}benzoic acid methyl ester was suspended in ethanol (30 mL) and sodium hydroxide (4 N, 8.1 mL) was added. The reaction mixture was stirred overnight. The mixture was concentrated to dryness, suspended in water (100 mL), acidified with hydrochloric acid (8.5 mL, 4 N) and extracted with ethyl acetate (100 mL). The aqueous phase was extracted once more with ethyl acetate (30 mL) and the combined organic phases were washed with water (3×50 mL), dried with magnesium sulphate and concentrated in vacua. The residue was crystallised from a mixture of ethyl acetate and n-heptane to afford 1.75 g of 4-{[tert-butoxycarbonyl-(4-cyclohexylphenyl)amino]methyl}-benzoic acid.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe aqueous phase was extracted once more with ethyl acetate (30 mL)
  4. washthe combined organic phases were washed with water (3×50 mL)
  5. dry with materialdried with magnesium sulphate
  6. concentrationconcentrated in vacua
  7. customThe residue was crystallised from a mixture of ethyl acetate and n-heptane

Sources & evidence

ORD record
ord-d59122890e2840c4b33592887555211d
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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