Citric Acid → HCID 17805852, compound

HRID 365698Notes

Reaction equation

HRID 365698 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:9]=[C:8]([CH2:23][O:24]C(=O)C)[N:7]=1)(=O)C.C(OCC1C=C(CCC2C=CC([N+]([O-])=O)=CC=2)C=C(C)N=1)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[OH:24][CH2:23][C:8]1[CH:9]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:11]=[C:6]([CH2:5][OH:4])[N:7]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 232929272-Pyridinemethanol, 6-methyl-4-[2-(4-nitrophenyl)ethyl]-, 2-acetateHCID 57103833HCID 57103833, compound

Product 1

HCID 17805852HCID 17805852, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diacetate (7) (12.0 g, 34.1 mmol), was dissolved in 50 ml of ethanol. To this solution stirred at RT, sodium hydroxide 5 H, 20 ml was added at once. After 10 min, when the TLC test for the substrate was negative, the mixture was neutralized with citric acid, and partitioned between sat. sodium hydrogen carbonate and ethanol/chloroform 1:1. The extraction was repeated three times using 100 ml of organic solvent for each extraction. The combined extracts were evaporated and the residual mixture was flash chromatographed using finally 8% ethanol/ chloroform as a solvent. The appropriate pure fractions were collected and evaporated.

Workup

  1. custompartitioned between sat. sodium hydrogen carbonate and ethanol/chloroform 1:1
  2. extractionThe extraction
  3. extractionfor each extraction
  4. customThe combined extracts were evaporated
  5. customchromatographed
  6. customThe appropriate pure fractions were collected
  7. customevaporated

Sources & evidence

ORD record
ord-2b5d97dedaba41d6b61869be5f96df69
Source dataset
uspto-grants-2000_10
Patent number
US06127529

Reaction notes

Loading…