2,4-Dichlorobenzyl chloride → HCID 69989841, compound

HRID 1018699Notes

Reaction equation

HRID 1018699 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C@H:4]([CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Cl:20][C:21]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:22]=1[CH2:23]Cl.CCN(CC)CC>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[C@H:4]([CH2:13][C:14]1[N:18]=[CH:17][N:16]([CH2:23][C:22]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:21]=2[Cl:20])[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 8471TriethylamineHCID 178501431HCID 178501431, compound

Product 1

HCID 69989841HCID 69989841, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(tert-butoxycarbonyl)-L-histidine methyl ester (1.0 g) was added to a solution of 2,4-dichlorobenzyl chloride (0.73 g) and Et3N (0.27 g) in benzene (10 ml) and the mixture was heated under reflux for 1 hr. The mixture was cooled and the precipitate was removed by filtration. The filtrate was washed with H2O, dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluent; 95:5, CHCl3/MeOH) to give N-(tert-butoxycarbonyl)-1-[(2,4-dichlorophenyl)methyl]-L-histidine methyl ester. The obtained compound was treated in a similar manner as described in R. Example 4 to give 1-[(2,4-Dichlorophenyl)methyl]-L-histidine methyl ester, dihydrochloride salt.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureThe mixture was cooled
  4. customthe precipitate was removed by filtration
  5. washThe filtrate was washed with H2O
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by column chromatography on silica gel (eluent; 95:5, CHCl3/MeOH)

Sources & evidence

ORD record
ord-955a3f5a0adc46e99b403b826a683e47
Source dataset
uspto-grants-2002_11
Patent number
US06482849B1

Reaction notes

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