Methyl iodide → HCID 22844256, compound

HRID 1197001Notes

Reaction equation

HRID 1197001 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:33]([OH:35])=[O:34])[C:10]([S:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[C:38](=O)([O-])O.[K+]>CN(C)C=O>[CH3:38][O:34][C:33](=[O:35])[C@@H:9]([C:10]([S:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([CH3:12])[CH3:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 22844255N-(tert-Butoxycarbonyl)-3-[(triphenylmethyl)sulfanyl]-D-valine

Product 1

HCID 22844256HCID 22844256, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of N-t-butoxycarbonyl-S-trityl-D-penicillamine (A-2) (6.0 g) in dimethylformamide (40 ml), were added methyl iodide (1.5 ml) and potassium hydrogencarbonate (2.4 g), and the mixture was stirred for 14 hours. To the reaction mixture was added ice-water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated saline, and dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, to give N-t-butoxycarbonyl-S-trityl-D-penicillamine methyl ester (6.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated saline, and dried over magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-0fe72926178d4e1d915d96f3657ab157
Source dataset
uspto-grants-1992_05
Patent number
US05116861

Reaction notes

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