dibenzyl 4-[N,N-bis(2-chloroethyl)amino]phenylcarbamoyl-L-glutamate → 4-[N,N-bis-(2-chloroethyl)amino]phenylcarbamoyl-L-glutamic acid

HRID 861221Notes

Reaction equation

HRID 861221 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH:8]([C:31]([O:33]CC1C=CC=CC=1)=[O:32])[CH2:9][C@@H:10]([C:21]([O:23]CC1C=CC=CC=1)=[O:22])[NH:11][C:12](=[O:20])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][CH2:6][Cl:7]>CN(C=O)C.[Pd]>[Cl:1][CH2:2][CH2:3][N:4]([CH:8]([C:31]([OH:33])=[O:32])[CH2:9][C@@H:10]([C:21]([OH:23])=[O:22])[NH:11][C:12](=[O:20])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][CH2:6][Cl:7]

Participants

4

Reactant 1

HCID 70224102dibenzyl 4-[N,N-bis(2-chloroethyl)amino]phenylcarbamoyl-L-glutamate

Product 1

HCID 702240994-[N,N-bis-(2-chloroethyl)amino]phenylcarbamoyl-L-glutamic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of the intermediate dibenzyl 4-[N,N-bis(2-chloroethyl)amino]-phenylcarbamoyl-L-glutamate (1.138 g) in DMF (15 ml) was hydrogenated over 10% Pd/C for 16 hours. After filtration and evaporation in vacuo, the residue was dissolved in CHCl3 (20 ml). After 18 hours the crystalline precipitate was filtered off and dried in vacuo to obtain 4-[N,N-bis-(2-chloroethyl)amino]phenylcarbamoyl-L-glutamic acid. Yield, 730 mg (93%). After recrystallisation from acetone/CHCl3 microscopic rods formed m.p. 116°-118° C. NMR (CD3 COCD3): δ8.0(s)1H; 7.2(d)2H; 6.6(d)2H; 6.2(d)2H NH; 4.4(m)1H; 3.6(m)8H; 2.5-1.9(m)4H.

Workup

  1. filtrationAfter filtration and evaporation in vacuo
  2. dissolutionthe residue was dissolved in CHCl3 (20 ml)
  3. filtrationAfter 18 hours the crystalline precipitate was filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d91295500e70409ab9ad3637d53b6fd4
Source dataset
uspto-grants-1998_02
Patent number
US05714148

Reaction notes

Loading…