Ammonium Hydroxide → HCID 9884861, compound

HRID 1531868Notes

Reaction equation

HRID 1531868 reaction equation
[C:1]1(=[O:26])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.C[N:28](C1C=CC=CN=1)C.[OH-].[NH4+]>O>[C:1]1(=[O:26])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=2)[CH2:7][C:8]([NH2:28])=[O:9])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 218852-DimethylaminopyridineHCID 9798625HCID 9798625, compound

Product 1

HCID 9884861HCID 9884861, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-phthalimido-3(4-propoxyphenyl)propionic acid (1.41 g, 4.0 mmol) in 25 mL of under nitrogen was added carbonyldlimidazole (0.68 g, 4.2 mmol) followed by a catalytic amount of dimethylaminopyridine. The mixture was stirred for 45 minutes at room temperature. To the reaction mixture was then added concentrated ammonium hydroxide (0.29 mL, 4.4 mmol) and the reaction mixture was stirred for 30 minutes at room temperature. The mixture was then diluted with 10 mL of water and the tetrahydrofuiran was removed in vacuo. The resulting slurry was filtered and the solid was washed with copious amounts of water. The solid was dried in vacuo (60° C., <1 mm) to afford 1.2 g of crude product. The crude product was purified by dissolving in 200 mL of ethyl acetate, stirring for 3h and then concentrating to an 80 mL volume. The resulting slurry was filtered and the solid was washed with ethyl acetate (2×20 mL). The solid was air-dried to afford 0.513 g (36%) of 3-phthalimido-3-(4-propoxyphenyl)propionamide as a white powder: mp 109.5-110.4° C.; 1H NMR (DMSO-d6, 250 MHz) δ7.85 (br s, 4H), 7.55 (br s, 1H), 7.33 (d, 2H, J=8 Hz), 6.75-7.00 (m, 3H), 5.69 (t, 2H, J=8 Hz), 3.88 (t, 2H J=6 Hz), 3.10-3.30 (m, 2H), 1.60-1.80 (m, 2H), 0.95 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ171.2, 167.7, 158.0, 134.5, 131.23, 131.19, 128.4, 123.1, 114.3, 68.9, 49.9, 36.9, 22.0, 20.4, 10.4; Anal. Calcd. for C20N2O40.37 H2O. Theoretical: C, 66.90; H, 5.61; N, 7.80. Found: C, 66.90; H, 5.52; N, 7.75.

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  2. customthe tetrahydrofuiran was removed in vacuo
  3. filtrationThe resulting slurry was filtered
  4. washthe solid was washed with copious amounts of water
  5. customThe solid was dried in vacuo (60° C., <1 mm)
  6. customto afford 1.2 g of crude product
  7. customThe crude product was purified
  8. dissolutionby dissolving in 200 mL of ethyl acetate
  9. stirringstirring for 3h
  10. concentrationconcentrating to an 80 mL volume
  11. filtrationThe resulting slurry was filtered
  12. washthe solid was washed with ethyl acetate (2×20 mL)
  13. customThe solid was air-dried

Sources & evidence

ORD record
ord-28515abf11764a6caef077a42c99db37
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

Loading…