HCID 19091797, compound → HCID 19091840, compound

HRID 488251Notes

Reaction equation

HRID 488251 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]([C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[H][H]>[Pd].C1COCC1.C(OCC)(=O)C>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][N:6]([C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:24])[CH3:12]

Participants

6

Reactant 2

HCID 19091797HCID 19091797, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19091840HCID 19091840, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.3 g of N-(3-nitrobenzoyl)-N-(2-ethoxy-2-oxoethyl) glycine ethyl ester and 0.5 g of 10% palladium on carbon in 40 ml THF and 40 ml ethyl acetate was stirred in a hydrogen atmosphere for 16 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to an oil which was purified by HPLC using 50% ethyl acetate-hexane to remove an impurity and ethyl acetate to elute 3.1 g of N-(3-aminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester as an oil. The nmr and mass spectra were consistent with the structure.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to an oil which
  3. customwas purified by HPLC
  4. customto remove an impurity and ethyl acetate
  5. washto elute 3.1 g of N-(3-aminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester as an oil

Sources & evidence

ORD record
ord-e1185873cd1441ecb2f537c3b137886c
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…