Trimethylsilyldiazomethane → 2-(3-Methoxycarbonyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester

HRID 1754923Notes

Reaction equation

HRID 1754923 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([O:12][C:13]([N:15]1[CH2:34][CH2:33][C:18]2([N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([OH:31])=[O:30])[CH:24]=3)[NH:20][C:19]2=[O:32])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CO>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][C:18]2([N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([O:31][CH3:1])=[O:30])[CH:24]=3)[NH:20][C:19]2=[O:32])[CH2:33][CH2:34]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 66818237HCID 66818237, compound

Product 1

HCID 668184592-(3-Methoxycarbonyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Trimethylsilyl)diazomethane (2.0 M in hexane, 4.0 ml, 8.0 mmol) was added dropwise to a solution of 2-(3-carboxy-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (200 mg, 0.54 mmol) in methanol (10 ml). The mixture was stirred at room temperature for one hour, and (trimethylsilyl)diazomethane (1.0 ml, 2.0 mmol) was then further added, followed by stirring for one hour. The reaction mixture was concentrated under reduced pressure, and the resulting solid was then washed with a solution of hexane/ethyl acetate=5/1 to give 2-(3-methoxycarbonyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (91.5 mg, 44%).

Workup

  1. stirringby stirring for one hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washthe resulting solid was then washed with a solution of hexane/ethyl acetate=5/1

Sources & evidence

ORD record
ord-eded67fe921944f89f485755cfd6f155
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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