Triethylamine → HCID 21285525, compound

HRID 2417499Notes

Reaction equation

HRID 2417499 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7]O.CS(Cl)(=O)=O.C(N(CC)CC)C.Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27].C(=O)([O-])O.[Na+]>ClCCl.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][NH:31][CH2:30][C:29]([O:28][CH2:26][CH3:27])=[O:32]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 12016493(5-Fluoro-2-nitrophenyl)methanol

Product 1

HCID 21285525HCID 21285525, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.8 g (10.7 mmol) of 5-fluoro-2-nitrobenzyl alcohol was dissolved in 20 ml of dichloromethane. 0.9 ml (12.8 mmol) of methanesulfonyl chloride and 2.2 ml (16.1 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 20 ml of ethanol. 1.79 g (12.8 mmol) of glycine ethyl ester hydrochloride and 1.35 g (16.1 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid. The obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.

Workup

  1. stirringwere stirred at 70° C. for 6 hours
  2. customThe solvent was evaporated
  3. extractionAfter the extraction with ethyl acetate
  4. washthe extract was washed with 1 N hydrochloric acid
  5. extractionAfter the extraction with ethyl acetate
  6. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  7. customdried
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6f2202b40e22458694dd4c2dd4b15479
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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