Trimethyl orthoformate → Methyl 4-sulfamoylbutanoate

HRID 597797Notes

Reaction equation

HRID 597797 reaction equation
[S:1]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:4])(=[O:3])[NH2:2].[CH3:11]OC(OC)OC>CO>[CH3:11][O:9][C:8](=[O:10])[CH2:7][CH2:6][CH2:5][S:1](=[O:4])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 27733204-sulfamoylbutanoic Acid

Product 1

HCID 10511613Methyl 4-sulfamoylbutanoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-sulfamoylbutyric acid (2.53 g, 15.1 mmol), methanol (25 ml), trimethylorthoformate (10 ml, approx 5 eq) and polystyrene-bound toluenesulfonic acid (0.58 g) was stirred at 60° C. After 19 h the mixture was decantated from the catalyst and concentrated to yield 2.70 g (99%) of the title ester as an oil.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-f2568c9d82e64416af584b71990b1591
Source dataset
uspto-grants-2011_03
Patent number
US07897560B2

Reaction notes

Loading…