HCID 86734393, compound → HCID 21485347, compound

HRID 1414851Notes

Reaction equation

HRID 1414851 reaction equation
[CH3:1]S.[C:3]([NH:6][C:7](SC)([CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=[O:5])[CH3:4]>[Ni].CC(C)=O>[C:3]([NH:6][CH:7]([CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[C:8]([O:10][CH3:1])=[O:9])(=[O:5])[CH3:4]

Participants

4

Reactant 1

HCID 86734393HCID 86734393, compound

Product 1

HCID 21485347HCID 21485347, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 180AcetoneSolvent

Procedure

Four (4.0) cc of Raney nickel was suspended in 15 ml of acetone, and stirred for 2 hours at room temperature to be deactivated. To the system then 417 mg of 2-acetylamino-2-methylthio-5,5-dimethoxyvaleric acid methanethiol was added, followed by 18 hours' stirring at room temperature. After removing the insoluble matter by filtration, the filtrate was concentrated under reduced pressure. The residue was parted by a column chromatography (silica gel and ethyl acetate), to provide 310 mg of methyl 2-acetylamino-5,5-dimethoxyvalerate as a colorless oil. The yield was 89%.

Workup

  1. waitfollowed by 18 hours
  2. stirring' stirring at room temperature
  3. customAfter removing the insoluble matter
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aaa72d80e3c24b92b859671434ab3869
Source dataset
uspto-grants-1977_01
Patent number
US04002682

Reaction notes

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