Benzoyl chloride → (S)-3-(Benzoylaminomethyl)-5-methylhexanoic acid

HRID 48537Notes

Reaction equation

HRID 48537 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH2:13][C@H:14]([CH2:19][NH2:20])[CH2:15][C:16]([OH:18])=[O:17])[CH3:12]>C1COCC1>[C:1]([NH:20][CH2:19][C@@H:14]([CH2:13][CH:11]([CH3:12])[CH3:10])[CH2:15][C:16]([OH:18])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 5486971Pregabalin

Product 1

HCID 9813903(S)-3-(Benzoylaminomethyl)-5-methylhexanoic acidYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl chloride (0.88 ml, 7.6 mmol) was added to a stirred suspension of pregabalin (1.0 g, 6.3 mmol) in THF (80 ml) at room temperature under argon and the reaction mixture was stirred for 18 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was chromatographed (SiO2, heptane-ethyl acetate, 1:1 to 3:7) to give 4 (0.78 g, 47%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed (SiO2, heptane-ethyl acetate, 1:1 to 3:7)

Sources & evidence

ORD record
ord-9eada8501a9241f8bf39909cddae410d
Source dataset
uspto-grants-2004_03
Patent number
US06703522B2

Reaction notes

Loading…