Water → 4-Hexyl-3-[(4-methoxycarbonylphenyl)methyl]aminobenzoic acid morpholide

HRID 2734

Reaction equation

HRID 2734 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[O:6].[CH3:22][O:23][C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)=[O:25].O>C(O)(=O)C>[CH2:16]([C:15]1[CH:14]=[CH:13][C:4]([C:5]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)=[O:6])=[CH:3][C:2]=1[NH:1][CH2:30][C:29]1[CH:28]=[CH:27][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 539494553-Amino-4-hexylbenzoic acid morpholide

Product 1

HCID 867517094-Hexyl-3-[(4-methoxycarbonylphenyl)methyl]aminobenzoic acid morpholide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound ([5]-(55)-75) (600 mg) prepared in Example 63 was dissolved in acetic acid (6.0 ml). Then, 4-methoxycarbonylbenzaldehyde (373 mg) was added. The mixture was stirred at room temperature for 4 hours. Then, boranediethylamine complex (146 mg) was added to the solution. The mixture was stirred at room temperature for 30 minutes. After the reaction was completed, water was added to the solution. The solution was extracted with ethyl acetate, washed with distilled water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=30 g, hexane/ethyl acetate=1/1) to obtain the above-captioned compound ([5]-(57)-75') (841 mg) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. extractionThe solution was extracted with ethyl acetate
  3. washwashed with distilled water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Kieselgel 60=30 g, hexane/ethyl acetate=1/1)
  7. customto obtain the above-captioned compound ([5]-(57)-75') (841 mg) as a white solid

Sources & evidence

ORD record
ord-20fb073b44614d5f8991584cce60fb11
Source dataset
uspto-grants-1998_03
Patent number
US05731310

Linked notes

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