HCID 18738447, compound → 3-((dimethylamino)sulfonyl]-2(R)-methylpropionic acid

HRID 1934466Notes

Reaction equation

HRID 1934466 reaction equation
[CH3:1][N:2]([CH3:19])[S:3]([CH2:6][C@H:7]([CH3:18])[C:8]([O:10]CC1C=CC=CC=1)=[O:9])(=[O:5])=[O:4]>C(O)(=O)C.[Pd]>[CH3:19][N:2]([CH3:1])[S:3]([CH2:6][C@H:7]([CH3:18])[C:8]([OH:10])=[O:9])(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 18738447HCID 18738447, compound

Product 1

HCID 187384363-((dimethylamino)sulfonyl]-2(R)-methylpropionic acidYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A 100 mL Fisher/Porter vessel was charged with 1.4 g of benzyl 3-[(dimethylamino)sulfonyl]-2(R)-methylpropionate in 30 mL acetic acid with a catalytic amount of 10% Pd—C. The reaction was hydrogenated at 50 psi for 24 hours, filtered through Celite and concentrated in vacuo. The residue was azeotroped with toluene then concentrated in vacuo to afford 900 mg of 3-[(dimethylamino)sulfonyl]-2(R)-methylpropionic acid which was used without further purification.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was azeotroped with toluene
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-686b36f125654dfea51f842c304663dd
Source dataset
uspto-grants-2002_05
Patent number
US06384036B1

Reaction notes

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