Methyl iodide → HCID 18753515, compound

HRID 1838409Notes

Reaction equation

HRID 1838409 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[CH2:9]([O:12][C:13](=[O:45])[CH:14]([CH2:32][CH2:33][N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44])[NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:10]=[CH2:11]>CN(C)C=O>[CH2:9]([O:12][C:13](=[O:45])[CH:14]([CH2:32][CH2:33][N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44])[N:15]([CH3:3])[S:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][CH:24]=1)(=[O:17])=[O:18])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18753652HCID 18753652, compound

Product 1

HCID 18753515HCID 18753515, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.83 g, 5.8 mmol) and potassium carbonate (5.34 g, 38.4 mmol) were added to a solution of (±)-N-(4-phenoxybenzenesulfonyl)-2-(2-phthalimidoethyl)glycine allyl ester (2.00 g, 3.8 mmol), the product of (2) above, in N,N-dimethylformamide (20 ml). This mixture was stirred at room temperature for 1 hour. The insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=3/1 as the eluant to afford the desired compound (1.90 g, yield 93%) as a colorless oil.

Workup

  1. customThe insoluble material was removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-5b7486a2300c44038a6638b65b30ecfa
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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