1,4-Dioxane → HCID 67099883, compound

HRID 1868802Notes

Reaction equation

HRID 1868802 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15](OCC)=[O:16])=[C:5]2[OH:20].Cl.[C:22]([O:26][C:27](=[O:31])[C@H:28]([CH3:30])[NH2:29])([CH3:25])([CH3:24])[CH3:23].O1CCOCC1.C(N(C(C)C)C(C)C)C>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])([CH3:13])[C:7](=[O:14])[C:6]([C:15]([NH:29][C@H:28]([C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:31])[CH3:30])=[O:16])=[C:5]2[OH:20]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 11275390tert-Butyl alaninate hydrochlorideHCID 67099655HCID 67099655, compound

Product 1

HCID 67099883HCID 67099883, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To ethyl 6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (2.44 g, 8.28 mmol, see Example 2) and L-alanine t-butyl ester hydrochloride (2.26 g, 12.4 mmol), were added 1,4-dioxane (5.52 mL) and N-ethyl-N-isopropylpropan-2-amine (4.33 mL, 24.8 mmol). The reaction mixture was then heated in a microwave at 140° C. for 10 minutes. The reaction mixture was diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 3 times with 50 mL of NaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (0.815 g) as a light yellow amorphous solid after flash chromatography. MS (m/z)=338(M+H-tBu)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with NaHCO3 (saturated, aqueous)
  3. washwashed 3 times with 50 mL of NaHCO3 (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dade1db01c9445f4a93f50c06f39bca5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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