HCID 18915883, compound → HCID 18915882, compound

HRID 1379625Notes

Reaction equation

HRID 1379625 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([O:9][C:10]([NH:12][CH2:13][CH2:14][S:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:11])[CH3:8]>O.CO>[CH2:7]([O:9][C:10]([NH:12][CH2:13][CH2:14][S:15]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:2])=[O:11])[CH3:8]

Participants

5

Reactant 2

HCID 18915883HCID 18915883, compoundHCID 23667635Sodium periodate

Product 1

HCID 18915882HCID 18915882, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

There was dissolved 149.7 g (0.7 mol) of sodium metaperiodate in 1400 ml of water, and thereto was added dropwise a solution of 164.5 g (0.7 mol) of ethyl 2-[2-(ethoxycarbonylamino)ethylthio]acetate in 125 ml of methanol under cooling with ice. After dropping the mixture was stirred for 7 hours under cooling with ice. The precipitate was removed by filtration and washed with water and with chloroform, successively. The filtrate was extracted with chloroform and dried over anhydrous sodium sulfate. Then the solvent was removed under reduced pressure to give 138.6 g of white solid. The solid was recrystallized from ethanol-n-hexane (1:4) to give 113.5 g of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customThe precipitate was removed by filtration
  4. washwashed with water and with chloroform
  5. extractionThe filtrate was extracted with chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThen the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6a3e2ab8c205427183cb65f9d8f6a0cb
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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