Trimethylsilyldiazomethane → N-Boc-allylglycine methyl ester

HRID 230324Notes

Reaction equation

HRID 230324 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([N:15]([CH2:20][CH:21]=[CH2:22])[CH2:16][C:17]([OH:19])=[O:18])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>ClCCl.CO>[CH3:1][O:18][C:17](=[O:19])[CH2:16][N:15]([CH2:20][CH:21]=[CH2:22])[C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 10330883Boc-N-(Allyl)-Glycine

Product 1

HCID 22243128N-Boc-allylglycine methyl ester

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Trimethylsilyldiazomethane (2N, in hexane) (12 ml) was added dropwise to a solution of N-Boc-allylglycine (3.09 g) in dichloromethane/methanol (2/1) mixture (30 ml), and the resulting mixture was stirred at room temperature for 3 hours. After concentrating the reaction solution, the residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=20/1-10/1) to obtain N-Boc-allylglycine methyl ester (3.11 g). NMR (H1, CDCl3): δ 2.43-2.55 (2H, m), 3.72 (3H, s), 4.34-4.39 (1H, brm), 5.02 (1H, brs), 5.09-5.13 (2H, m), 5.62-5.72 (1H, m)

Workup

  1. concentrationAfter concentrating the reaction solution
  2. customthe residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=20/1-10/1)

Sources & evidence

ORD record
ord-96e70257c8b1401cbf2d3c5f908ec921
Source dataset
uspto-grants-2009_07
Patent number
US07566724B2

Reaction notes

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