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Hydrochloric Acid → HCID 22708149, compound

HRID 353178
Notes
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Reaction equation

HRID 353178 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 176
Acetic Acid
Solvent
HCID 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-b9567585f4ee466f84eaa5bfb7dd068e
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06750236B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes