Oxalic Acid → HCID 15713272, compound

HRID 847381Notes

Reaction equation

HRID 847381 reaction equation
[C:1]1(S([O-])(=O)=O)[CH:6]=CC=CC=1.[CH:11]([C:13]1C=C[N+](C)=CC=1)=[O:12].C(Cl)Cl.[N+](=C1C[CH2:34][CH2:33][CH2:32][C:31]2[CH:26]1CCC[CH:30]=2)=[N-].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].CN(C)C=[O:45]>>[OH:38][C:37]1([C:36]([O:41][CH2:6][CH3:1])=[O:40])[CH2:26][CH:31]([CH3:30])[CH2:32][CH:33]([C:34]([O:12][CH2:11][CH3:13])=[O:45])[O:39]1

Participants

6

Reactant 5

HCID 971Oxalic AcidHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 98171274-Formyl-1-methylpyridinium benzenesulfonateHCID 22747271HCID 22747271, compound

Product 1

HCID 15713272HCID 15713272, compound

Procedure

840 mg of 4-formyl-1-methyl pyridinium benzensulfonate were added to a solution of 740 mg of the product of Step A, 15 ml of methylene chloride and 5 ml of dimethylformamide and the reaction mixture was stirred for 45 minutes. 1 ml of diazobicyclo[5,4,0]-undec-7-ene was added and the reaction mixture was stirred for 45 minutes. After cooling down to 5°-10° C., 5 ml of a saturated aqueous solution of oxalic acid were added and the reaction mixture was stirred for 1 hour. Extraction took place with methylene chloride followed by washing with a solution of sodium bicarbonate, drying, filtering and bringing to dryness to obtain 630 mg of product which was chromatographed on silica, eluting with a cyclohexane-ethyl acetate (9-1) mixture to obtain 160 mg of Isomer A and 125 mg of Isomer B.

Workup

  1. stirringthe reaction mixture was stirred for 45 minutes
  2. temperatureAfter cooling down to 5°-10° C.
  3. stirringthe reaction mixture was stirred for 1 hour
  4. extractionExtraction
  5. washby washing with a solution of sodium bicarbonate
  6. customdrying
  7. filtrationfiltering

Sources & evidence

ORD record
ord-15f3565efd3f459c8ec06b2aeebe4a3e
Source dataset
uspto-grants-1992_08
Patent number
US05141952

Reaction notes

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