Methyl iodide → HCID 57036803, compound

HRID 975692Notes

Reaction equation

HRID 975692 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@@H:8]1[CH2:32][C:33](=[S:35])[NH2:34])=[O:6])[CH:2]=[CH2:3].IC.[C:38](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@@H:8]1[CH2:32][C:33](=[NH:34])[S:35][CH3:38])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86750461HCID 86750461, compound

Product 1

HCID 57036803HCID 57036803, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2R,4S)-1-allyloxycarbonyl-2-thiocarbamoylmethyl-4-(triphenylmethylthio) pyrrolidine (110 mg) in acetonitrile (4 ml) were added iodomethane (497 mg) and potassium carbonate (61 mg). After stirring at room temperature for 3 hours, the solution was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with aqueous sodium chloride solution, dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica gel (eluent; n-hexane:ethyl acetate=3:2) to give (2R,4S)-1-allyloxycarbonyl-2-(2-imino-2-methylthioethyl)-4(triphenylmethylthio) pyrrolidine (72 mg).

Workup

  1. washThe separated organic layer was washed with aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-5c8b3c59d68f47c08f9bc62244c013fb
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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