Sodium Chloride → 3-{4-[(4-Tert-butylphenylamino)methyl]benzoylamino}propionic acid methyl ester

HRID 1633955Notes

Reaction equation

HRID 1633955 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(OCC)(OCC)OCC.C([BH3-])#N.[Na+].[C:32]([C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33].[Cl-].[Na+]>CN(C=O)C.C(O)(=O)C>[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:40][C:39]2[CH:41]=[CH:42][C:36]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:37][CH:38]=2)=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 31214Ethyl orthoformateHCID 698614-Tert-ButylanilineHCID 5003444Sodium cyanoborohydrideHCID 161003253-(4-Formylbenzoylamino)propionic acid methyl ester

Product 1

HCID 161003413-{4-[(4-Tert-butylphenylamino)methyl]benzoylamino}propionic acid methyl esterYield 30%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The above 3-(4-formylbenzoylamino)propionic acid methyl ester (2.0 g, 8.5 mmol) was dissolved in DMF (20 mL). Triethyl orthoformate (10 mL), glacial acetic acid (1 mL), sodium cyanoborohydride (0.81 g, 12.8 mmol) and 4-tert-butylaniline 1.27 g, 8.5 mmol) were added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was added saturated aqueous sodium chloride (100 mL) and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were 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 (1:1) to afford 0.87 g (30%) of 3-{4-[(4-tert-butylphenylamino)methyl]benzoylamino}propionic acid methyl ester as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride (3×100 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and heptane (1:1)

Sources & evidence

ORD record
ord-476916ddc9e54c038baab9b6c2ce9b1a
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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