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

HRID 1477370Notes

Reaction equation

HRID 1477370 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 160695741-Benzyl 4-(tert-Butyl) N-Benzyl-N-[2-(iodomethyl)allyl]-L-aspartateYield 88.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-6e344eda9fbe49aa908c7080ca0e0435
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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