Trimethylsilyldiazomethane → HCID 43147866, compound

HRID 2067961Notes

Reaction equation

HRID 2067961 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH3:14][Si](C=[N+]=[N-])(C)C>>[CH3:14][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1

Participants

3

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 6036193-Amino-3-(3-bromophenyl)propanoic acid

Product 1

HCID 43147866HCID 43147866, compoundYield 95%

Procedure

To a solution of 3-amino-3-(3-bromo-phenyl)-propionic acid (1.0 g, 4.1 mmol) in methanol-toluene (100 mL; 1:1 solution) at room temperature is added trimethylsilyl diazomethane (2.0 M solution in hexanes, 20 mL, 40 mmol). After 30 min, excess trimethylsilyl diazomethane is quenched by addition of glacial acetic acid (5 mL). Concentration in vacuo affords of 3-amino-3-(3-bromo-phenyl)-propionic acid methyl ester (1.0 g, 95%) as a colorless liquid which solidifies upon standing.

Workup

  1. customexcess trimethylsilyl diazomethane is quenched by addition of glacial acetic acid (5 mL)
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-6469d99b38774976955b57419cf219c2
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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