Acetic Acid → HCID 53878395, compound

HRID 1814681Notes

Reaction equation

HRID 1814681 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1.C(O)(=O)C.C([BH3-])#N.[Na+].[CH2:26]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[CH2:27][CH2:28][CH3:29]>CN(C=O)C.C(OCC)(OCC)OCC>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:34][C:33]2[CH:35]=[CH:36][C:30]([CH2:26][CH2:27][CH2:28][CH3:29])=[CH:31][CH:32]=2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 76944-ButylanilineHCID 5003444Sodium cyanoborohydrideHCID 161003253-(4-Formylbenzoylamino)propionic acid methyl ester

Product 1

HCID 53878395HCID 53878395, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 31214Ethyl orthoformateSolvent

Procedure

The above propionic acid methyl ester (2.0 g, 8.5 mmol) was dissolved in DMF (20 mL) and triethyl orthoformate (10 mL), glacial acetic acid (1 mL), sodium cyanoborohydride (0.81 g, 12.8 mmol) and 4-butylaniline 1.27 g, 8.5 mmol) were added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (100 mL) and washed with saturated aqueous sodium chloride (3×100 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and heptane (3:1) to afford 1.54 g (49%) of 3-{4-[(4-butylphenylamino)methyl]-benzoylamino}propionic acid methyl ester as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aqueous sodium chloride (3×100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and heptane (3:1)

Sources & evidence

ORD record
ord-82c28eeba3534bc8901d8a2a5ca8e79b
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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