Glycine tert-butyl ester hydrochloride → HCID 67099648, compound

HRID 2078112Notes

Reaction equation

HRID 2078112 reaction equation
[C:1]([C:3]1([CH3:20])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[C:5]([C:14](OCC)=[O:15])[C:4]1=[O:19])#[N:2].Cl.[C:22]([O:26][C:27](=[O:30])[CH2:28][NH2:29])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1>[C:1]([C:3]1([CH3:20])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[C:5]([C:14]([NH:29][CH2:28][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:30])=[O:15])[C:4]1=[O:19])#[N:2]

Participants

4

Reactant 2

HCID 2725036Glycine tert-butyl ester hydrochloride2×HCID 67099896HCID 67099896, compound

Product 1

HCID 67099648HCID 67099648, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-cyano-4-hydroxy-1-methyl-2-oxo-naphthalene-3-carboxylate (0.225 g, 0.829 mmol), glycine tert-butyl ester hydrochloride (0.167 g, 0.995 mmol), and glycine tert-butyl ester hydrochloride (0.167 g, 0.995 mmol) were refluxed in dioxane (50 mL) for 14 hours. The solvent was then removed in vacuo. The resulting residue was concentrated in vacuo and purified using silica flash chromatography (10-40% EtOAc/hexanes). MS (m/z)=301 (M+H)+(hydrolyzed product) 379.1 (product+Na).

Workup

  1. customThe solvent was then removed in vacuo
  2. concentrationThe resulting residue was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-c0969eea403f4f9baf8faa5cc0249eea
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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