Water → HCID 15521678, compound

HRID 351627Notes

Reaction equation

HRID 351627 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])[CH3:11].O.CN([CH:22]=[O:23])C>>[CH2:10]([O:12][C:13](=[O:17])[C@@H:14]([NH:15][C:22]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)=[O:23])[CH3:16])[CH3:11]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 133964-AminobenzonitrileHCID 76507L-Alanine ethyl ester

Product 1

HCID 15521678HCID 15521678, compound

Procedure

A solution of 4-aminobenzonitrile (2.3 g, 0.0195 mol) and N,N′-carbonyldiimidazole (3.5 g, 0.332 mol) in DMF (20 ml) was heated at 80° C. for 7 hours (h). A solution of L-alanine ethyl ester (3 g, 0.0195 mol) in DMF (15 ml) was added and stirring was continued for 3 days (d) at 80° C. Water (300 ml) was added and the precipitate was filtered off (giving 750 mg of the dimer as side product). The solution was extracted with ethyl acetate to give 3 g of the title compound which contained the corresponding acid as side product. MS (mass spectrometry) peak was at 262.1 (M+1)+.

Workup

  1. customat 80° C
  2. filtrationthe precipitate was filtered off (
  3. customgiving 750 mg of the dimer as side product)
  4. extractionThe solution was extracted with ethyl acetate

Sources & evidence

ORD record
ord-3bacf1ab429947d585d98f14728dd504
Source dataset
uspto-grants-2004_06
Patent number
US06743790B2

Reaction notes

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