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

HRID 8832Notes

Reaction equation

HRID 8832 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-8439c1cf79f4464094398af5231f416d
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

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