Hydrochloric Acid → HCID 22708149, compound

HRID 1266512Notes

Reaction equation

HRID 1266512 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:6][CH:5]=1.[CH:21](=O)[C:22]1[O:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+].Cl>CO.C(O)(=O)C>[O:26]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:21][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7362FurfuralHCID 5003444Sodium cyanoborohydrideHCID 11623510Tert-butyl 2-(4-(2-aminoethyl)phenylthio)-2-methylpropanoate

Product 1

HCID 22708149HCID 22708149, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4.0 g of 1,1-dimethylethyl 2-[[4-(2-aminoethyl)phenyl]thio]-2-methyl-propanoate [(P. J. Brown et al., J. Med. Chem. 42, 3785-88 (1999)] are dissolved in 100 ml of methanol and treated with 2.6 g of furfural. 9.3 ml of glacial acetic acid are added and the mixture is boiled briefly (10 min). The mixture is then cooled to 0° C., and 4.25 g of sodium cyanoborohydride are added a little at a time. The mixture is then stirred at room temperature overnight. 1 N HCl is added until the mixture is acidic, and the mixture is stirred for 30 min. The mixture is concentrated slightly and made basic using sat. NaHCO3 solution. The mixture is then extracted twice with ethyl acetate and the extracts are washed (sat. NaCl solution) and dried and concentrated. Chromatographic purification (dichloromethane/methanol 15+1) gives 2.4 g of the title compound as a colourless oil.

Workup

  1. custombriefly (10 min)
  2. stirringthe mixture is stirred for 30 min
  3. concentrationThe mixture is concentrated slightly
  4. extractionThe mixture is then extracted twice with ethyl acetate
  5. washthe extracts are washed (sat. NaCl solution)
  6. customdried
  7. concentrationconcentrated
  8. customChromatographic purification (dichloromethane/methanol 15+1)

Sources & evidence

ORD record
ord-ba61f9b29c6f4acc90ff22468a7be0e9
Source dataset
uspto-grants-2003_04
Patent number
US06548538B2

Reaction notes

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