HCID 10555862, compound → HCID 10575129, compound

HRID 1654323Notes

Reaction equation

HRID 1654323 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][C:9]=1[Cl:41])[CH2:5][CH2:6][Cl:7]>C(OCC)(=O)C.[Pd]>[Cl:7][CH2:6][CH2:5][N:4]([C:8]1[CH:13]=[CH:12][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:10][C:9]=1[Cl:41])[CH2:3][CH2:2][Cl:1]

Participants

4

Reactant 1

HCID 10555862HCID 10555862, compound

Product 1

HCID 10575129HCID 10575129, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of dibenzyl N-((4[N,N-bis-(2-chloroethyl)amino]3-chlorophenylcarbamoyl))-L-glutamate (350 mg) in ethyl acetate (30ml) containing 30% palladium on carbon 70mg (50% moist) was stirred under an atmosphere of hydrogen for 1 hour. After filtration of the catalyst the filtrate was evaporated to dryness and the residue triturated with ether/ethyl acetate to obtain N-(4-[N,N-bis (2-chloroethyl)amino]-3-chlorophenylcarbamoyl)-L glutamic acid as an oil. NMR: 8.7 (s) 1H; 7.6 (s) 1H; 7.1-7.4 (m) 2H; 6.5 (d) 1H; 4.2 (m) 1H; 3.3-3.6 (m) 8H; 1.7-2.4 (m) 4H.

Workup

  1. filtrationAfter filtration of the catalyst the filtrate
  2. customwas evaporated to dryness
  3. customthe residue triturated with ether/ethyl acetate

Sources & evidence

ORD record
ord-d67876e971354a4fa1278c7a59cfef19
Source dataset
uspto-grants-1995_04
Patent number
US05405990

Reaction notes

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