Methanol → HCID 22632621, compound

HRID 2417470Notes

Reaction equation

HRID 2417470 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13]Br)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].CO.[CH3:17]N(C1C=CC=CN=1)C.Cl.[CH2:27]([O:29][C:30](=[O:33])[CH2:31][NH2:32])[CH3:28].C(=O)([O-])O.[Na+]>ClCCl.C1COCC1>[CH2:27]([O:29][C:30]([CH2:31][NH:32][CH2:13][C:12]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:17])=[O:8])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])=[O:33])[CH3:28]

Participants

8

Reactant 5

HCID 887MethanolHCID 218852-DimethylaminopyridineHCID 1323864-Bromomethyl-3-nitrobenzoic acidHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 22632621HCID 22632621, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (9.6 mmol) of 3-nitro-4-bromomethylbenzoic acid was dissolved in 100 ml of dichloromethane. 0.78 ml (19.2 mmol) of methanol, 2.2 g (11.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-3-carbodiimide hydrochloride and 30 mg of dimethylaminopyridine were added to the obtained solution, and they were stirred at room temperature for 3 hours. The reaction mixture was treated with dichloromethane as the extracting solvent by an ordinary method to obtain the crude product. The crude product was dissolved in 50 ml of THF. 2.0 g (14.6 mmol) of glycine ethyl ester hydrochloride and 1.8 g (21.9 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 80° C. for 4 hours. The insoluble matter was removed by the filtration, and the solvent was evaporated. After the extraction with ethyl acetate followed by the treatment by an ordinary method, the crude title compound was obtained.

Workup

  1. customto obtain the crude product
  2. stirringwere stirred at 80° C. for 4 hours
  3. customThe insoluble matter was removed by the filtration
  4. customthe solvent was evaporated
  5. extractionAfter the extraction with ethyl acetate

Sources & evidence

ORD record
ord-4d65a7bf1b094ce7a67e50fdb4a8dcaf
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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