Oxalyl chloride → Valproic Acid

HRID 1802903Notes

Reaction equation

HRID 1802903 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([C:8](N)=[O:9])[CH2:5][CH2:6][CH3:7].C(Cl)(=O)C(Cl)=[O:13].C1C(/C=C/[N+]([O-])=O)=CC(O)=C(O)C=1>ClCCCl>[C:8]([OH:9])(=[O:13])[CH:4]([CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 71113ValpromideHCID 64391581,2-dihydroxy-4-(nitroethenyl)benzene

Product 1

HCID 3121Valproic Acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of valpromide (3.0 g, 20.95 mmol) in DCE (30 mL) at 0-5° C. was added oxalyl chloride (1.3 mL, 15.08 mmol) and refluxed overnight. The reaction mixture was cooled to RT, a solution of SL-1 (0.808 g, 5.24 mmol) in DCE (3 mL) was added and stirred overnight. After usual work-up and chromatographic purification, 1.97 g (43%) of I-AA-MPD22 were obtained as a white solid. 1H NMR (CDCl3, 300 MHz): δ 0.89 (t, 12H, J=7.18 Hz), 1.28-1.66 (m, 16H), 2.94-2.95 (m, 2H), 3.02 (t, 6H, J=6.51 Hz), 4.42 (t, 4H, J=6.47 Hz). MS: m/z 493.2 [M+H]+, 510.0 [M+NH4]+, 515.10 [M+Na]+.

Workup

  1. temperaturerefluxed overnight
  2. customAfter usual work-up and chromatographic purification, 1.97 g (43%) of I-AA-MPD22
  3. customwere obtained as a white solid

Sources & evidence

ORD record
ord-c310252de94e459cae4a08c25c1976e6
Source dataset
uspto-grants-2013_01
Patent number
US08349901B2

Reaction notes

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