1,1'-Carbonyldiimidazole → HCID 21250940, compound

HRID 1417380Notes

Reaction equation

HRID 1417380 reaction equation
[C:1]1([CH:7]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)([N:24]1C=CN=C1)=O>O1CCCC1>[C:1]1([CH:7]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:21])[CH2:8][C:9]([NH2:24])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 188709533-(1-Oxo-1,3-dihydro-isoindole-2-yl)-3-phenyl-propionic acid

Product 1

HCID 21250940HCID 21250940, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-phenyl-3-(1-oxoisoindolin-2-yl)propionic acid (0.703 g, 2.50 mmol) in 15 mL of tetrahydrofuran under nitrogen was added carbonyldiimidazole (0.438 g, 2.70 mmol), and a few crystals of 4-N,N-dimethylaminopyridine [DMAP]. The reaction mixture was stirred for 1.5 hours and then 0.25 mL of 15N ammonium hydroxide was added. After 20 minutes, the reaction mixture was concentrated in vacuo and the residue slurried in water. The resulting solid was isolated by filtration and dried in vacuo to afford 0.58 g (80%) of crude product as an off-white powder. The crude product was recrystallized from ethanol to afford 0.403 g (57%) of 3-phenyl-3-(1-oxoisoindolin-2-yl)propionamide as white prisms: 1H NMR (DMSO-d6, 250 MHz) 7.8-7.2 (m, 10 H), 6.92 (br s, 1 H), 5.81 (overlapping dd, 1 H) 4.59 (d, J=17.5 Hz, 1 H), 4.16 (d, J=17.5 Hz, 1 H), 3.1-2.8 (m, 2 H); 13C NMR (DMSO-d6) 171.3, 167.0, 140.7, 132.2, 131.4, 128.6, 127.9, 127.5, 126.9, 123.5, 122.8, 51.5, 46.3, 37.9; Anal. Calcd for C17H16N2O2 : Theory C, 72.84; H, 5.75; N, 9.99. Found: C, 72.46; H, 5.68; N, 9.91.

Workup

  1. waitAfter 20 minutes
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe resulting solid was isolated by filtration
  4. customdried in vacuo
  5. customto afford 0.58 g (80%) of crude product as an off-white powder
  6. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-fa9fcccc731c4e7fac719844e5d81c01
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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