Pentanoic Acid → HCID 68809240, compound

HRID 2105630Notes

Reaction equation

HRID 2105630 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)(=O)C(C)(C)C.[Cl-].[Li+].[CH:17]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[NH:21]1)([CH3:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C(N(CC)CC)C>[C:1]([N:21]1[C@@H:20]([CH:17]([CH3:19])[CH3:18])[CH2:24][O:23][C:22]1=[O:25])(=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

9

Reactant 5

HCID 7991Pentanoic AcidHCID 10340Sodium CarbonateHCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

Product 1

HCID 68809240HCID 68809240, compoundYield 96.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-10 °C

Procedure

Under an atmosphere of nitrogen, to a mixed solution of tetrahydrofuran (383 ml) (hereinafter, abbreviated as THF) and triethylamine (88 ml) was added valeric acid (38 g) and dissolved. To the mixture was dropped pivaloyl chloride (45 ml) at −15° C. to −10° C. The reaction mixture was stirred at −10° C. for 1 hour, and thereto was added anhydrous lithium chloride (12 g). To the mixture was added a solution of (S)-4-isopropyl-2-oxazolidinone (32.3 g) in THF (118 ml), and the reaction mixture was stirred at 25° C. for 15 hours. To the mixture were added an saturated aqueous solution of sodium carbonate and water, and the mixture was stirred for 18 hours. To the reaction mixture were added water, a mixed solvent (n-heptane:ethyl acetate=2:1) (300 ml) and aqueous solution of sodium hydroxide (2 N) (100 ml), and the mixture was extracted. The aqueous layer was extracted with a mixed solvent (n-heptane:ethyl acetate=2:1). The combined organic layer was washed with water, hydrochloric acid (3 N), water, an saturated aqueous solution of sodium bicarbonate, and brine sequentially. The obtained organic layer was dried over anhydrous magnesium sulfate, and filtrated and concentrated to give the title compound (51.5 g) having the following physical data.

Workup

  1. dissolutiondissolved
  2. stirringthe reaction mixture was stirred at 25° C. for 15 hours
  3. stirringthe mixture was stirred for 18 hours
  4. extractiona mixed solvent (n-heptane:ethyl acetate=2:1) (300 ml) and aqueous solution of sodium hydroxide (2 N) (100 ml), and the mixture was extracted
  5. extractionThe aqueous layer was extracted with a mixed solvent (n-heptane:ethyl acetate=2:1)
  6. washThe combined organic layer was washed with water, hydrochloric acid (3 N), water
  7. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2f8f365adbdc46f2b014f31de83235ac
Source dataset
uspto-grants-2009_08
Patent number
US07579375B2

Reaction notes

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