Water → HCID 18780708, compound

HRID 1417405Notes

Reaction equation

HRID 1417405 reaction equation
[C:1]1(=[O:30])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[C:13]([O:21][CH:22]([CH3:24])[CH3:23])[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.[OH-].[NH4+:32].O>CN(C)C1C=CN=CC=1.O1CCCC1>[C:1]1(=[O:30])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[C:13]([O:21][CH:22]([CH3:24])[CH3:23])[CH:12]=2)[CH2:7][C:8]([NH2:32])=[O:9])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12

Participants

6

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 18780709HCID 18780709, compound

Product 1

HCID 18780708HCID 18780708, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-phthalimido-3-(3,4-diisopropoxyphenyl)propionic acid (1.0 g, 2.4 mmol), 1,1 carbonyldiimidazole (0.43 g, 2.6 mmol), and 4-dimethylaminopyridine (trace) in tetrahydrofuran (18 mL) was stirred for 1.5 hours at room temperature. To the solution was added ammonium hydroxide (0.24 mL, 3.7 mmol, 28-30%) and stirring was continued for 2 hours. The tetrahydrofuran was removed in vacuo leaving an oil. To the oil was added 2 mL of water and the mixture was stirred at room temperature overnight. The resulting slurry was filtered, the solid was washed with water, air dried, and dried in vacuo (60° C., <1 mm) to afford 0.87 g (88%) of 3-phthalimido-3-(3,4-diisopropoxyphenyl)propionamide as a white solid: mp 153°-154.5° C.; 1H NMR (DMSO-d6) δ 7.92-7.78 (m, 4H), 7.55 (s, 1H), 7.03(s, 1H), 6.93-6.77 (m, 3H), 5.71-5.56 (m, 1H), 4.51-4.33 (m, 2H), 3.25-3.06 (m, 2H), 1.31-1.08 (m, 12H); 13C NMR (DMSO-d6) δ 171.7, 168.3, 148.9, 133.9, 132.1, 131.9, 123.3, 120.9, 117.7, 72.2, 72.1, 51.5, 37.9, 22.2; Anal. Calcd. for C23H26N2O5. Theoretical: C, 67.30; H, 6.38; N, 6.82. Found: C, 67.01; H, 6.35; N, 6.69.

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. customleaving an oil
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationThe resulting slurry was filtered
  5. washthe solid was washed with water, air
  6. customdried
  7. customdried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-2568d288eeca41bfae114e3ec0958c4b
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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