Ammonium Hydroxide → HCID 9884861, compound

HRID 1940071Notes

Reaction equation

HRID 1940071 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(N1C=CN=C1)([N:29]1C=CN=C1)=O.CN(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]([NH2:29])=[O:9])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 218852-DimethylaminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 9798625HCID 9798625, compound

Product 1

HCID 9884861HCID 9884861, compoundYield 36.4%

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 carbonyldiimidazole (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 tetrahydrofuran 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 3 h 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, 1H, 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 C20N2O4 0.37 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 tetrahydrofuran 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 3 h
  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-60487684ca9b48b5b87bf1e488e5fc71
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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