Water → HCID 22932162, compound

HRID 1351089Notes

Reaction equation

HRID 1351089 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][NH2:5].[CH3:6][CH:7]([CH3:21])[C:8](=O)[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=S.C(N(CC)CC)C.O>C(#N)C>[CH2:13]([O:12][C:10]1[CH:9]=[C:8]([CH:7]([CH3:21])[CH3:6])[N:4]([CH2:3][CH2:2][OH:1])[N:5]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80172-HydrazinoethanolHCID 8471TriethylamineHCID 22932184HCID 22932184, compound

Product 1

HCID 22932162HCID 22932162, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Hydroxyethylhydrazine (1.90 g) was added to a solution of O-Benzyl 4-methyl-3-oxothiopentanoate (5.90 g) and triethylamine (5.05 g) in acetonitrile (60 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give the title compound (5.90 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c00c74838268406e860fe4bd3e52d014
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

Loading…