Oxalic Acid → HCID 20085581, compound

HRID 1608836Notes

Reaction equation

HRID 1608836 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][CH2:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1)(=[O:10])=[O:9].[C:19]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([CH3:22])([CH3:21])[CH3:20].[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>CO.C(OCC)(=O)C>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[NH:18]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:13][CH2:12][NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][CH:31]=[C:23]([C:19]([CH3:21])([CH3:20])[CH3:22])[CH:24]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 20085601HCID 20085601, compoundHCID 221431023-tert-Butylbenzoyl chloride

Product 1

HCID 20085581HCID 20085581, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 1C using 2.80 g (0.0107 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl] benzene sulfonamide and 4.20 g (0.0213 mol) of meta-t-butylbenzoyl chloride with the exception that, after reducing the reaction solution to dryness under reduced pressure the resultant residue was dissolved in methanol. The resulting solution was heated to reflux for approximately one hour and then reduced to dryness under reduced pressure. The resultant residue was redissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated and the organic layer was washed with water and then a saturated sodium chloride solution, dried over anhydrous sodium sulfate and then reduced to dryness under reduced pressure. The resultant residue was purified using preparatory high performance liquid chromatography (8000 ml of a gradient of methylene chloride to 10% methanol and 0.5% ammonium hydroxide in methylene chloride). Fractions containing the free base form of the desired titled compound were combined and then reduced to dryness under reduced pressure to provide an oil. This oil was dissolved in methanol and 0.36 g of oxalic acid were added, with stirring. The resulting solution was reduced to dryness under reduced pressure to provide a foam. This foam was crystallized from a 1:10 solution of methanol/ethyl acetate to provide 1.74 g of the desired titled compound (m.p. 191°-193.5° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for approximately one hour
  4. customThe resulting layers were separated
  5. washthe organic layer was washed with water
  6. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  7. customThe resultant residue was purified
  8. additionFractions containing the free base form of the desired titled compound
  9. customto provide an oil
  10. customto provide a foam
  11. customThis foam was crystallized from a 1:10 solution of methanol/ethyl acetate

Sources & evidence

ORD record
ord-26db5f0516e446eea4b345cdd955208c
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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