Methyl iodide → HCID 54329215, compound

HRID 375744Notes

Reaction equation

HRID 375744 reaction equation
[NH2:1][C@H:2]([C:35]([O:37][CH3:38])=[O:36])[CH2:3][S:4][CH2:5][C:6]1[C:24]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:23][C:22]([O:33][CH3:34])=[CH:21][C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:9].[CH3:39]I>C(#N)C.C(OCC)(=O)C>[CH3:38][O:37][C:35]([C@@H:2]([NH:1][CH3:39])[CH2:3][S:4][CH2:5][C:6]1[C:24]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])=[CH:23][C:22]([O:33][CH3:34])=[CH:21][C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)=[O:9])=[O:36]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 53826829HCID 53826829, compound

Product 1

HCID 54329215HCID 54329215, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.90 g of p-nitrobenzyl (R)-2-[[[2-amino-2-methoxycarbonyl-ethyl]thio]methyl]-3-(tert-butyldimethylsilyloxy)-5-methoxybenzoate and 0.91 g of methyl iodide in 5 ml of acetonitrile was stirred at room temperature for 3 hours. The solution was diluted with ethyl acetate and washed successively with saturated sodium bicarbonate solution and with brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. The residual oil was chromatographed on silica gel using ethyl acetate/hexane (1:1, v/v) as eluent to yield 0.52 g of p-nitrobenzyl (R)-2-[[[2-methoxycarbonyl-2-(methylamino)ethyl]thio]methyl]-3-(tert-butyldimethylsilyloxy)-5-methoxybenzoate as an oil.

Workup

  1. washwashed successively with saturated sodium bicarbonate solution and with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-40056c4fc6074df488709c9c9221715c
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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