Sodium Iodide → 1-Benzyl 4-(tert-Butyl) N-Benzyl-N-[2-(iodomethyl)allyl]-L-aspartate

HRID 2240485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240485
[CH2:1]([N:8]([CH2:28][C:29]([CH2:31]Cl)=[CH2:30])[C@@H:9]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-:34]>CC(C)=O>[CH2:1]([N:8]([CH2:28][C:29]([CH2:31][I:34])=[CH2:30])[C@@H:9]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 160695541-Benzyl 4-(tert-Butyl) N-Benzyl-N-(2-(chloromethyl)allyl)-L-aspartate

Produkt 1

HCID 160695741-Benzyl 4-(tert-Butyl) N-Benzyl-N-[2-(iodomethyl)allyl]-L-aspartateAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyl 4-tert-butyl(2S)-2-{benzyl[2-(chloromethyl)prop-2-en-1-yl]amino}succinate from step 1b (8.7 g) and NaI (8.0 g) in acetone (100 mL) was stirred at RT overnight. The solid was filtered off and the filtrate concentrated. The residue was treated with methylene chloride and filtered through a pad of silica gel to give 1-benzyl 4-tert-butyl(2S)-2-{benzyl[2-(iodomethyl)prop-2-en-1-yl]amino}succinate (9.2 g). MS (ESI): 550.2 (M+H+).

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate concentrated
  3. additionThe residue was treated with methylene chloride
  4. filtrationfiltered through a pad of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ec6de78f8e994e99b7792c37334bd908
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723349B2

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