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

HRID 473754Notes

Reaction equation

HRID 473754 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-3467e796ec1144e1b3672a7f14f4d946
Source dataset
uspto-grants-2014_01
Patent number
US08637497B2

Reaction notes

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