benzyl 3-aminosulfonyl-2(R)-methylpropionate → 3-aminosulfonyl-2(R)-methylpropionic acid

HRID 8830Notes

Reaction equation

HRID 8830 reaction equation
[NH2:1][S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9]CC1C=CC=CC=1)=[O:8])(=[O:4])=[O:3]>CO.[Pd]>[NH2:1][S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([OH:9])=[O:8])(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 18738444benzyl 3-aminosulfonyl-2(R)-methylpropionate

Product 1

HCID 187384353-aminosulfonyl-2(R)-methylpropionic acidYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 100 mL Fisher/Porter vessel was charged with 1.1 g of crude benzyl 3-aminosulfonyl-2(R)-methylpropionate in 35 mL MeOH and a catalytic amount of 10% Pd—C. The mixture was hydrogenated at 50 psi for 24 hours, filtered through Celite and concentrated in vacuo to yield 700 mg of 3-aminosulfonyl-2(R)-methylpropionic acid as a clear oil. The crude acid was used without further purification.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-201cd0be739148328f976d03ae2a2f3d
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

Loading…