Water → HCID 66818075, compound

HRID 1755094Notes

Reaction equation

HRID 1755094 reaction equation
I[CH3:2].[OH-].[Na+].[C:5]([O:9][C:10]([N:12]1[CH2:23][CH2:22][C:15]2([NH:19][C:18](=[S:20])[NH:17][C:16]2=[O:21])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O>CO>[C:5]([O:9][C:10]([N:12]1[CH2:13][CH2:14][C:15]2([N:19]=[C:18]([S:20][CH3:2])[NH:17][C:16]2=[O:21])[CH2:22][CH2:23]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 86672794HCID 86672794, compound

Product 1

HCID 66818075HCID 66818075, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodomethane (0.329 ml, 5.28 mmol) and a 1 N aqueous NaOH solution (3.3 ml, 3.3 mmol) were sequentially added to a solution of 4-oxo-2-thioxo-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (944 mg, 3.3 mmol) in methanol (33 ml) at room temperature, and the mixture was stirred at the same temperature overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layers were combined and dried over magnesium sulfate, and the solvent was then distilled off. The residue was purified by silica gel column chromatography to give 2-methylsulfanyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (762 mg, 77%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd109a688e2741c59142903653dacb1f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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