Water → HCID 18780708, compound

HRID 1421323Notes

Reaction equation

HRID 1421323 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), 4.514.33 (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-277c222b7f97495fa8ff4a0c01d48723
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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