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

HRID 1856729Notes

Reaction equation

HRID 1856729 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-33d6e8107c6644c1b5a33ee8c2ea1431
Source dataset
uspto-grants-2000_11
Patent number
US06143747

Reaction notes

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