2,4-Dichlorobenzyl chloride → HCID 69989841, Verbindung

HRID 1358594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358594
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 69989841HCID 69989841, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-bffab852faf34ffb8b40c06b1f428474
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596752B1

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