Diethyl Ether → HCID 9907022, compound

HRID 1417396Notes

Reaction equation

HRID 1417396 reaction equation
[C:1]1(=[O:24])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.C(N1C=CN=C1)([N:27]1C=CN=C1)=O.[OH-].[NH4+].CCOCC>O1CCCC1.CN(C)C1C=CN=CC=1>[C:1]1(=[O:24])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:7][C:8]([NH2:27])=[O:9])[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 10737463HCID 10737463, compound

Product 1

HCID 9907022HCID 9907022, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-phthalimido-3-(3,4-dichlorophenyl)propionic acid (1.10 g, 3.02 mmol) in 20 mL of tetrahydrofuran at room temperature under nitrogen was added carbonyldiimidazole (0.51 g, 3.17 mmol) and a catalytic amount of 4-dimethylaminopyridine. The mixture was stirred for 45 in and then concentrated ammonium hydroxide (0.21 mL, 3.2 mmol) was added. The reaction mixture was stirred for 10 minutes and then the tetrahydrofuran was removed under reduced pressure. To the resulting mixture was added 20 mL of water, a light yellow oil was formed. To the mixture was added 3 mL of ether, the mixture was stirred at room temperature for 1 hour. The resulting slurry was filtered, the solid was washed with water and air-dried to afford 0.73 g of the crude product as a white solid. The crude product was purified by flash chromatography (silica gel hexane/methylene chloride, 22-0% (v/v)) to afford 0.39 g (36%) of 3-phthalimido-3-(3,4-dichlorophenyl)propionamide as a white powder: 1H NMR (DMSO-d6, 250 MHz) δ 7.83 (m, 4 H, Ar), 7.35-7.75 (m, 4 H), 6.93 (br s, 1 H), 5.72 (t, 1 H, J=8 Hz), 3.25 (dd, 1 H, J1 =8 Hz, J2 =15 Hz), 3.14 (dd, 1 H, J1 =8 Hz, J2 =15 Hz); 13C NMR (DMSO-d6) δ 170.8, 167.6, 140.2, 134.6, 131.2, 131.0, 130.7, 130.3, 129.2, 127.7, 123.2, 49.3, 36.5. Anal. Calcd for C17H12N2O3Cl2. Theoretical C, 54.69; H, 3.54; N, 7.53. Found C, 54.69; H, 3.38; N, 7.15.

Workup

  1. additionwas added
  2. customthe tetrahydrofuran was removed under reduced pressure
  3. additionTo the resulting mixture was added 20 mL of water
  4. customa light yellow oil was formed
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. filtrationThe resulting slurry was filtered
  7. washthe solid was washed with water
  8. customair-dried
  9. customto afford 0.73 g of the crude product as a white solid
  10. customThe crude product was purified by flash chromatography (silica gel hexane/methylene chloride, 22-0% (v/v))

Sources & evidence

ORD record
ord-6297a10fcd0544f59f2689f0f033d2eb
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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