Methyl iodide → HCID 67408509, compound

HRID 1174380Notes

Reaction equation

HRID 1174380 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[C:10](=O)([O-])[O-].[K+].[K+].CI.[C:18](=O)([O:34]N1C(=O)CCC1=O)[O:19][CH2:20][CH:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2>O1CCOCC1.O>[CH:32]1[C:33]2[CH:21]([CH2:20][O:19][C:18]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([S:6][CH3:10])([CH3:5])[CH3:4])=[O:34])[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]=2[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 92863L-PenicillamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Product 1

HCID 67408509HCID 67408509, compoundYield 137.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of L-penicillamine (0.60 g, 4.02 mmol) in mixture of water (20 mL) and dioxane (20.0 mL) at room temperature were added potassium carbonate (11.04 g, 79.9 mmol) and methyl iodide (0.31 mL, 4.98 mmol), and the mixture was stirred for 1 hour. 9−fluorenylmethyl succinimidyl carbonate (5.39 g, 16.0 mmol) was added, and the reaction was stirred at room temperature for 12 hours. The reaction was evaporated, and the residue was partitioned between ether and water, and the mixture was adjusted to pH 3 with 2 N HCl. The organic was washed with brine and dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient starting with dichloromethane and ending with 10% methanol in dichloromethane to give the product (2.13 g).

Workup

  1. stirringthe reaction was stirred at room temperature for 12 hours
  2. customThe reaction was evaporated
  3. customthe residue was partitioned between ether and water
  4. washThe organic was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica gel eluting with a gradient

Sources & evidence

ORD record
ord-4a2d22daa6c6463e87bc9973a04b42e9
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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