Hydrochloric Acid → HCID 21842659, compound

HRID 1737409Notes

Reaction equation

HRID 1737409 reaction equation
N#N.[O-][Mn](=O)(=O)=O.[K+].[OH:9][CH2:10][CH2:11][CH2:12][C:13]1[C:18]2[O:19][C@@H:20]([CH2:23][O:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH2:21][O:22][C:17]=2[CH:16]=[CH:15][C:14]=1[N+:35]([O-:37])=[O:36].S(=O)(O)[O-:39].[Na+].Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.O>[N+:35]([C:14]1[CH:15]=[CH:16][C:17]2[O:22][CH2:21][CH:20]([CH2:23][O:24][S:25]([C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)(=[O:27])=[O:26])[O:19][C:18]=2[C:13]=1[CH2:12][CH2:11][C:10]([OH:39])=[O:9])([O-:37])=[O:36]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 87918044HCID 87918044, compound

Product 1

HCID 21842659HCID 21842659, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 50 ml 3-neck flask equipped with magnetic stirrer, thermometer, N2 line and dropping funnel, was added KMnO4 (1.24 g, 9.25 mmole), H2O (15 ml) and tetra-n-butylammonium chloride (0.17 g). The purple solution was cooled to 0° C. and to it was added dropwise the (R)-toluene-4-sulfonic acid 8-(3-hydroxy-propyl)-7-nitro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (1.20 g, 2.84 mmole) prepared above in 10.3 ml of benzene. The reaction was stirred at room temperature overnight and then 4.40 g of sodium bisulfite was added. The color of the mixture was discharged after five minutes' stirring. After an addtional 10 minutes' stirring, 4 N isopropanolic HCl was added to bring the pH to about 1. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed four times with 50 ml of brine, dried over MgSO4, filtered and concentrated to yield a clear yellow oil (0.95 g, 77%) of 3-[6-nitro-3-(toluene-4-sulfonyloxymethyl)-2,3-dihydro-benzo[1,4]dioxin-5-yl]-propionic acid.

Workup

  1. customTo a 50 ml 3-neck flask equipped with magnetic stirrer
  2. waitThe color of the mixture was discharged after five minutes
  3. stirring' stirring
  4. stirringAfter an addtional 10 minutes' stirring
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed four times with 50 ml of brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1ee1d43dcfa044eca349fa0862171992
Source dataset
uspto-grants-1999_10
Patent number
US05962465

Reaction notes

Loading…