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

HRID 651203Notes

Reaction equation

HRID 651203 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-chloro-ethyl)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 (CD3COCD3): δ 8.0(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-26390d75a7574777a8ec9e8bf5d141be
Source dataset
uspto-grants-2001_08
Patent number
US06277880B1

Reaction notes

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