HCID 21505011, compound → HCID 21504998, compound

HRID 1076498Notes

Reaction equation

HRID 1076498 reaction equation
C([O:8][C:9](=[O:24])[CH:10]([O:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1.[H][H]>[Pd]>[C:16]([O:15][CH:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:24])=[O:8])(=[O:23])[C:17]1[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 21505011HCID 21505011, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21504998HCID 21504998, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

8.2 g of benzyl-(RS)-2-(isonicotinoyloxy)-isocaproate were hydrogenated in 50 ml of alcohol after the addition of 800 mg. of palladium-on-charcoal (5%) until the theoretical amount of hydrogen had been taken up. The catalyst was then filtered off and the filtrate evaporated under reduced pressure at 45°. The resulting oil was dissolved in excess sodium bicarbonate solution and extracted twice with 20 ml portions of ether and the bicarbonate solution adjusted to pH 2.5 with 3-N hydrochloric acid. The acidic solution was extracted twice with 70 ml portions of ethyl acetate. After being washed twice with 20 ml portions of 5% sodium chloride solution, the ethyl acetate solution was dried with magnesium sulphate and evaporated under reduced pressure at 45°. The resulting oil was crystallized from ether/petroleum ether to yield (RS)-2-(isonicotinoyloxy)-isocaproic acid; mp 98°-100°.

Workup

  1. additionafter the addition of 800 mg
  2. filtrationThe catalyst was then filtered off
  3. customthe filtrate evaporated under reduced pressure at 45°
  4. dissolutionThe resulting oil was dissolved in excess sodium bicarbonate solution
  5. extractionextracted twice with 20 ml portions of ether
  6. extractionThe acidic solution was extracted twice with 70 ml portions of ethyl acetate
  7. washAfter being washed twice with 20 ml portions of 5% sodium chloride solution
  8. dry with materialthe ethyl acetate solution was dried with magnesium sulphate
  9. customevaporated under reduced pressure at 45°
  10. customThe resulting oil was crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-204d0a9b3d5e454399da84decfbae51c
Source dataset
uspto-grants-1976_05
Patent number
US03957758

Reaction notes

Loading…