Sodium hydride → HCID 54747342, compound

HRID 553538Notes

Reaction equation

HRID 553538 reaction equation
[O:1]1CCC[O:3][CH:2]1[CH2:7][CH2:8][C:9]([C:11]1[C:12](=[O:36])[N:13]([CH3:35])[C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][CH:17]=[C:16]([C:22]1[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[CH:24][CH:23]=1)[CH:15]=2)=[O:10].C(OC(C1C=CC(C2C=C3C(C(O)=C(C(OC)=O)C(=O)N3C)=CC=2)=CC=1)=O)(C)(C)C.[H-].[Na+]>C1COCC1.CCOC(C)=O>[C:2]([CH2:7][CH2:8][C:9]([C:11]1[C:12](=[O:36])[N:13]([CH3:35])[C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][CH:17]=[C:16]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:33][CH:34]=1)[CH:15]=2)=[O:10])([OH:3])=[O:1]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 67406668HCID 67406668, compoundHCID 67410169Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 54747342HCID 54747342, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(3-(3-(1,3-dioxan-2-yl)propanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoate. Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (452 mg, 1104 μmol) was dissolved in THF (11 mL). Sodium hydride (60% in oil, 442 mg, 11040 μmol) was then added, and the resulting mixture was stirred at room temperature for 1 hour. 2-[2-(1,3-Dioxanyl)]ethylmagnesium bromide in THF (2208 μL, 1104 μmol) was then added dropwise, and the reaction mixture was then stirred for 1 hour. The reaction mixture was diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with 3 N HCl (aqueous), washed 2 times with 75 mL of brine (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotary evaporation to give initial product. The initial product was purified via flash chromatography (silica gel) to provide the title compound as a beige solid.

Workup

  1. stirringthe reaction mixture was then stirred for 1 hour
  2. additionadded to a separatory funnel
  3. custompartitioned with 3 N HCl (aqueous)
  4. washwashed 2 times with 75 mL of brine (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotary evaporation
  8. customto give initial product
  9. customThe initial product was purified via flash chromatography (silica gel)

Sources & evidence

ORD record
ord-b3746f10da65499abbad27a62d4a7afd
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

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