Diisopropylethylamine → HCID 67099588, compound

HRID 1868638Notes

Reaction equation

HRID 1868638 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[C:4](=[O:18])[C:3]=1[C:19](OCC)=[O:20].Cl.[C:25]([O:29][C:30](=[O:33])[CH2:31][NH2:32])([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C>O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=2)[C:5]([CH3:17])([CH3:16])[C:4](=[O:18])[C:3]=1[C:19]([NH:32][CH2:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:33])=[O:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099773HCID 67099773, compound

Product 1

HCID 67099588HCID 67099588, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of crude ethyl 4-hydroxy-1,1-dimethyl-2-oxo-6-(trifluoromethyl)-naphthalene-3-carboxylate (562 mg, 1712 μmol), glycine tert-butyl ester hydrochloride (316 mg, 1883 μmol) and DIPEA (447 μL, 2568 μmol) in 1,4-dioxane (20 mL) was heated to 120° C. in a sealed vessel. After 14 hours, the reaction was cooled to 23° C., and the solvent was removed under vacuum. The residue was diluted with EtOAc (100 mL), washed with water (75 mL) and brine (75 mL), dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (eluant: 4-8% EtOAc/hexane) affording 435 mg of the title compound. MS m/e=358.1 (M-C4H8+H)+.

Workup

  1. customthe solvent was removed under vacuum
  2. additionThe residue was diluted with EtOAc (100 mL)
  3. washwashed with water (75 mL) and brine (75 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography (eluant: 4-8% EtOAc/hexane)

Sources & evidence

ORD record
ord-7db01287d73546029af94c169feaa87d
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…