Triethylamine → HCID 22632516, compound

HRID 2417549Notes

Reaction equation

HRID 2417549 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([CH2:16]O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.Cl.[CH2:31]([O:33][C:34](=[O:37])[CH2:35][NH2:36])[CH3:32].C(=O)([O-])O.[Na+]>ClCCl.C(O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([CH2:16][NH:36][CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:37])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 22632504HCID 22632504, compound

Product 1

HCID 22632516HCID 22632516, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.4 g (5.6 mmol) of (1-benzyl-4-nitro-1H-pyrazol-3-yl)methanol was dissolved in 20 ml of dichloromethane. 0.53 ml (6.7 mmol) of methanesulfonyl chloride and 1.0 ml (7.3 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 50 ml of ethanol. 1.6 g (11.2 mmol) of glycine ethyl ester hydrochloride and 1.4 g (16.8 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. overnight. The insoluble matter was filtered. The solvent was evaporated and the residue was treated with ethyl acetate as the extracting solvent by an ordinary method, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. stirringwere stirred at 70° C. overnight
  2. filtrationThe insoluble matter was filtered
  3. customThe solvent was evaporated
  4. additionthe residue was treated with ethyl acetate as the extracting solvent by an ordinary method, which
  5. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-64e3d2288095415db14344160eb205b0
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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