Trimethyl orthovalerate → 4-[[2'-(t-Butyoxycarbonyl)biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

HRID 1742104Notes

Reaction equation

HRID 1742104 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22](=[S:25])[NH:23][NH2:24])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26](OC)(OC)(OC)[CH2:27][CH2:28][CH2:29][CH3:30]>COCCO>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][N:21]2[C:26]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:24][NH:23][C:22]2=[S:25])=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 10338402HCID 10338402, compound

Product 1

HCID 103201124-[[2'-(t-Butyoxycarbonyl)biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazole-3-thione

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 1.11 g (3.1 mmole) of 4-[[2'-(t-butoxycarbonyl)biphenyl-4-yl]methyl]-3-thiosemicarbazide and 792 μl (745 mg, 4.6 mmole) of trimethyl orthovalerate in 10 ml of 2-methoxyethanol was stirred at reflux under N2 for 15 hours. The cooled solution was concentrated, and the residue was purified by column chromatography on silica gel (gradient elution with 0-1% methanol in CH2Cl2) to give a gum which could be crystallized by trituration with petroleum ether. The product (828 mg, 63%, mp 135°-137° C.) was homogeneous by TLC in 19:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 424 (M+1).

Workup

  1. temperatureat reflux under N2 for 15 hours
  2. concentrationThe cooled solution was concentrated
  3. customthe residue was purified by column chromatography on silica gel (gradient elution with 0-1% methanol in CH2Cl2)
  4. customto give a gum which
  5. customcould be crystallized by trituration with petroleum ether

Sources & evidence

ORD record
ord-49f9d9bfc06a48f085a917f0d213f779
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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