Hydrochloric Acid → HCID 22708189, compound

HRID 353177Notes

Reaction equation

HRID 353177 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1)=O.[CH2:20]([NH2:26])[C:21]1[O:25][CH:24]=[CH:23][CH:22]=1.C([BH3-])#N.[Na+].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO.C(O)(=O)C>[O:25]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:20][NH:26][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3438FurfurylamineHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 22708158HCID 22708158, compound

Product 1

HCID 22708189HCID 22708189, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

550 mg of 1,1-dimethylethyl 2-[(4-formylphenyl)thio]-2-methyl-propanoate and 381 mg of furfurylamine are initially charged in 100 ml of methanol and treated with 1 ml of glacial acetic acid. The mixture is stirred at room temperature for 15 min, briefly brought to the boil and then, at 0° C., admixed a little at a time with 493 mg of sodium cyanoborohydride. The mixture is stirred overnight at room temperature and then treated with 1 N HCl and stirred for 30 min. The mixture is then made basic using Na2CO3 solution and extracted 2× with ethyl acetate. The organic phase is washed (sat. NaCl solution) and dried (MgSO4). Concentration and chromatographic purification (dichloromethane/ethyl acetate 10+1) gives 430 mg of a colourless oil.

Workup

  1. customat 0° C.
  2. stirringThe mixture is stirred overnight at room temperature
  3. stirringstirred for 30 min
  4. extractionextracted 2× with ethyl acetate
  5. washThe organic phase is washed (sat. NaCl solution)
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration and chromatographic purification (dichloromethane/ethyl acetate 10+1)

Sources & evidence

ORD record
ord-6a4d06378a7f4df0aa07b7e9bdc3edc8
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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