Methyl iodide → HCID 86751654, compound

HRID 2294719Notes

Reaction equation

HRID 2294719 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[S:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:34](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10](=[N:12][C@H:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[S:11][CH3:34])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86751653HCID 86751653, compound

Product 1

HCID 86751654HCID 86751654, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.1 g (2.43 mmol) of 4-benzyl 1-tert-butyl N-[(1-tert-butoxyformamido)thioacetyl]-L-aspartate, 1.95 ml of methyl iodide and 0.92 g of potassium carbonate in 50 ml of acetone is stirred at room temperature overnight. Thereafter, the solvent is distilled off under reduced pressure and the residue is taken up in ether. The organic phase is washed with water, dried over sodium sulphate and evaporated. 4-Benzyl 1-tert-butyl N-[2-(1-tert-butoxyformamido)-1-(methylthio)ethylidene]-L-aspartate is obtained as a mixture of the E- and Z-isomers; MS: 467 (M+H)+.

Workup

  1. distillationThereafter, the solvent is distilled off under reduced pressure
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-23b188f611e349828e16c81d14b32d2e
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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