HCID 22852790, compound → HCID 10363941, compound

HRID 2258402Notes

Reaction equation

HRID 2258402 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][C@H:18]([C:31]([O:33]CC2C=CC=CC=2)=[O:32])[CH2:19][CH2:20][C:21]([O:23]CC2C=CC=CC=2)=[O:22])=[O:16])=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7]>CN(C=O)C.[Pd]>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([NH:17][C@H:18]([C:31]([OH:33])=[O:32])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])=[CH:12][CH:13]=1)[CH2:5][CH2:6][Cl:7]

Participants

4

Reactant 1

HCID 22852790HCID 22852790, compound

Product 1

HCID 10363941HCID 10363941, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of dibenzyl N-(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 h. After filtration and evaporation in vacuo, the residue was dissolved in CHCl3 (20 ml). After 18 h the crystalline precipitate was filtered off and dried in vacuo to obtain N-(4-[N,N-bis-(2-chloroethyl)amino]phenylcarbamoyl)-L-glutamic acid. Yield, 730 mg (93%). After recrystallization from acetone/CHCl3 microscopic rods formed m.p. 116°-118°.

Workup

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

Sources & evidence

ORD record
ord-70b09ae5e20448c2ada945750b87ed42
Source dataset
uspto-grants-1997_08
Patent number
US05660829

Reaction notes

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