Water → HCID 23079525, compound

HRID 1365032Notes

Reaction equation

HRID 1365032 reaction equation
[CH2:1]([O:8][C:9](=S)[CH2:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH:18]([NH:21][NH2:22])([CH3:20])[CH3:19].C(N(CC)CC)C.O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[N:21]([CH:18]([CH3:20])[CH3:19])[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 22932184HCID 22932184, compound

Product 1

HCID 23079525HCID 23079525, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-methyl-3-oxothiopentanoic acid O-benzyl ester (0.84 g) and isopropylhydrazine hydrochloride (0.52 g) in acetonitrile (4 mL) was added triethylamine (1.4 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The solvent of the organic layer was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane/dichloromethane=1/1-2/3) to give the title compound (0.44 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. customThe solvent of the organic layer was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (hexane/dichloromethane=1/1-2/3)

Sources & evidence

ORD record
ord-e598949186b54a5786541f4b033c7998
Source dataset
uspto-grants-2011_02
Patent number
US07888487B2

Reaction notes

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