Formic Acid → HCID 10277899, compound

HRID 1581945Notes

Reaction equation

HRID 1581945 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([CH2:27][CH:28]([NH:38][OH:39])[CH2:29][CH2:30][C:31]3[CH:32]=[N:33][CH:34]=[C:35]([Cl:37])[CH:36]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][N:21]([S:24]([CH2:27][CH:28]([N:38]([OH:39])[CH:1]=[O:3])[CH2:29][CH2:30][C:31]3[CH:32]=[N:33][CH:34]=[C:35]([Cl:37])[CH:36]=3)(=[O:25])=[O:26])[CH2:22][CH2:23]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 21919406HCID 21919406, compound

Product 1

HCID 10277899HCID 10277899, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To formic acid (400 μl, 10.8 mmol) at 0° C. was added acetic anhydride (102 μl, 1.1 mmol) and the mixture was then stirred at RT for 15 minutes. The mixture was then re-cooled to 0° C., and a solution of 1-(4-chlorophenyl)-4-{[4-(5-chloropyridin-3-yl)-2-(hydroxyamino)butyl]sulfonyl}piperazine (100 mg, 0.22 mmol) in THF was added dropwise via syringe. After stirring at RT for 1.5 hours, volatiles were removed in vacuo, and the residue was azeotroped with toluene (2 mL). The residue was then dissolved in methanol (5 mL) and stirred at 40° C. for 1 hour. After cooling to RT, the solvent was evaporated, and the residue dissolved in methanol (0.5 mL). Diethyl ether (5 mL) was then added and the cloudy suspension stirred at RT for 1 hour. The solid that precipitated was filtered, washed with diethyl ether and dried in vacuo, to give the title compound as an off-white solid (48 mg, 0.099 mmol).

Workup

  1. temperatureThe mixture was then re-cooled to 0° C.
  2. stirringAfter stirring at RT for 1.5 hours
  3. customvolatiles were removed in vacuo
  4. customthe residue was azeotroped with toluene (2 mL)
  5. dissolutionThe residue was then dissolved in methanol (5 mL)
  6. stirringstirred at 40° C. for 1 hour
  7. temperatureAfter cooling to RT
  8. customthe solvent was evaporated
  9. dissolutionthe residue dissolved in methanol (0.5 mL)
  10. additionDiethyl ether (5 mL) was then added
  11. stirringthe cloudy suspension stirred at RT for 1 hour
  12. customThe solid that precipitated
  13. filtrationwas filtered
  14. washwashed with diethyl ether
  15. customdried in vacuo

Sources & evidence

ORD record
ord-43d86f6d2cdf49309cbd9c84554c4b4f
Source dataset
uspto-grants-2004_05
Patent number
US06734183B2

Reaction notes

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