Methyl iodide → HCID 67863591, compound

HRID 2073271Notes

Reaction equation

HRID 2073271 reaction equation
C(C[CH2:5][CH2:6]/[CH:7]=[CH:8]\[C@@H:9]1[CH2:13][C@@H:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][N:10]1[S:25]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])(O)=O.[H-].[Na+].I[CH3:38].[C:39]([O:42][CH2:43]C)(=[O:41])[CH3:40]>>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([S:25]([N:10]2[CH2:11][C@H:12]([N:14]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH3:38])[CH2:13][C@H:9]2/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:40][C:39]([O:42][CH3:43])=[O:41])(=[O:27])=[O:26])=[CH:33][CH:32]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 67863549HCID 67863549, compound

Product 1

HCID 67863591HCID 67863591, compound

Procedure

To a solution of (2S,4R)-2-[(Z)-5-carboxy-1-pentenyl]-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)pyrrolidine (274 mg) were added sodium hydride (60 mg) and iodomethane (0.1 ml) and the mixture was stirred at room temperature for 5 hours. The solution was diluted with ethyl acetate and washed successively with water and brine. The organic solution was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel with a mixture of n-hexane and ethyl acetate (3:1) as an eluent to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-[N-(4-chlorophenylsulfonyl)-N-methylamino]-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine (220 mg) as an oil.

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel with a mixture of n-hexane and ethyl acetate (3:1) as an eluent

Sources & evidence

ORD record
ord-0bd6797ad2dc471e902d7ad23f69d6e1
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

Loading…