Diisopropylethylamine → HCID 67099924, compound

HRID 2078284Notes

Reaction equation

HRID 2078284 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[C:8]([CH3:14])([CH3:13])[C:7](=[O:15])[C:6]([C:16](OCC)=[O:17])=[C:5]2[OH:21].Cl.[C:23]([O:27][C:28](=[O:31])[CH2:29][NH2:30])([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[C:8]([CH3:13])([CH3:14])[C:7](=[O:15])[C:6]([C:16]([NH:30][CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:31])=[O:17])=[C:5]2[OH:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099888HCID 67099888, compound

Product 1

HCID 67099924HCID 67099924, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 6-chloro-7-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.350 g, 1.12 mmol), glycine tert-butyl ester hydrochloride (0.244 g, 1.45 mmol), and Hunig's base (0.390 mL, 2.24 mmol) in 1,4-dioxane (15 mL) was heated at 120° C. for 2 hours in a sealed vessel. The solution was diluted with water (50 mL), extracted with EtOAc (2×50 mL), washed with water (50 mL), and then washed with brine (50 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica, 0-75% DCM in hexane) to give the title compound (0.305 g). MS m/e=396.5 (M−H)−.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washwashed with water (50 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica, 0-75% DCM in hexane)

Sources & evidence

ORD record
ord-ec20bd3b6ed847cf99d4049919f1c5c6
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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