Ammonium Hydroxide → 3-Phthalimido-3-(4-benzyloxy-3-methoxyphenyl)propionamide

HRID 1531876Notes

Reaction equation

HRID 1531876 reaction equation
[C:1]1(=[O:32])[N:5]([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:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12.C(N1C=CN=C1)([N:35]1C=CN=C1)=O.CN(C1C=CC=CN=1)C.[OH-].[NH4+]>>[C:1]1(=[O:32])[N:5]([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]([NH2:35])=[O:9])[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12

Participants

5

Reactant 4

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

Product 1

HCID 98455673-Phthalimido-3-(4-benzyloxy-3-methoxyphenyl)propionamideYield 65%

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 tetrahydrofuiran 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) δ7.84 (m, 4 H, 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) δ171.1, 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-f4dd5b7c0760407588f6d2cbf27393c7
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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