Ammonium Hydroxide → 3-(4-Benzyloxy-3-methoxy-phenyl)-propionamide

HRID 1421310Notes

Reaction equation

HRID 1421310 reaction equation
C1(=O)N([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:13]([O:25][CH3:26])[CH:12]=2)[CH2:7][C:8](O)=[O:9])C(=O)C2=CC=CC=C12.C(N1C=CN=C1)([N:35]1C=CN=C1)=O.CN(C1C=CC=CN=1)C.[OH-].[NH4+]>O1CCCC1>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:6][CH2:7][C:8]([NH2:35])=[O:9])=[CH:12][C:13]=1[O:25][CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 218852-DimethylaminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 98028103-Phthalimido-3-(4-benzyloxy-3-methoxyphenyl)propionic acid

Product 1

HCID 184425813-(4-Benzyloxy-3-methoxy-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-phthalimido-3-(4-benzyloxy-3-methoxyphenyl)propionic acid (1.00 g, 2.32 mmol), carbonyldiimidazole (0.406 g, 2.50 mmol) and a catalytic amount of dimethylaminopyridine in 20 mL of dry tetrahydrofuran under nitrogen was stirred for 1 hour. To the reaction solution was then added 0.25 mL of concentrated ammonium hydroxide. After 15 minutes, the reaction mixture was concentrated in vacuo to an oil which was diluted with 20 mL of water and stirred overnight. The resulting slurry was filtered and the solid dried to afford 0.645 g (65%) of 3-phthalimido-,3-(4-benzyloxy-3-methoxyphenyl)propionamide as a white powder: 1H NMR (DMSO-d6)δ 7.84 (m, 4H, Ar), 7.60-7.25 (m, 5H), 7.53 (br s, 1H, CONH), 7.15-6.8 (m, 4H), 5.67 (t, 1H, J=7.8 Hz), 5.04 (s, 2H, OCH2), 3.75 (s, 3H, OMe), 3.19 (d, 2H, J=9, 16.5 Hz);13C NMR (DMSO-d6)8 171.1, 167.6,148.8, 147.2, 137.0, 134.5, 132.0, 131.2, 128.3, 127.7, 127.6, 123.0, 119.3, 113.2, 111.4, 69.8, 55.5, 50.3, 36.9. Anal. Calcd for C25H22N2O5. Theory: C, 69.76; H, 5.15; N, 6.51. Found: C, 69.54; H, 5.13; N, 6.28.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo to an oil which
  2. additionwas diluted with 20 mL of water
  3. filtrationThe resulting slurry was filtered
  4. customthe solid dried

Sources & evidence

ORD record
ord-1e779b2bf7424b7a989812ae3a71b3c9
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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