Trimethylsilyldiazomethane → Methyl 6-ureidohexanoate

HRID 406300Notes

Reaction equation

HRID 406300 reaction equation
[NH:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:2]([NH2:4])=[O:3].[CH3:13][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[NH:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:2]([NH2:4])=[O:3]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 4605066-Ureidohexanoic acid

Product 1

HCID 43406503Methyl 6-ureidohexanoate

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

A solution of 6-ureidohexanoic acid (0.996 g, 5.72 mmol, 1.0 equiv) in methanol/benzene (2:7, 60 mL) was cooled to 0 degrees C., and a solution of trimethylsilyldiazomethane in hexanes (2.0 M, 3.43 mL, 6.86 mmol, 1.2 equiv) was added. The reaction mixture was warmed to room temperature and stirred for 1 h prior to removing all volatile components in vacuo. The crude methyl ester (1.06 g, 5.61 mmol, 98%) was used without further purification in the Biginelli reaction.

Workup

  1. customto removing all volatile components in vacuo

Sources & evidence

ORD record
ord-6de01cca02474f4c8adb12f3d6ae1cfa
Source dataset
uspto-grants-2014_06
Patent number
US08754094B2

Reaction notes

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