Water → HCID 86033953, compound

HRID 2378541Notes

Reaction equation

HRID 2378541 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:6][CH:7]=1.C([Li])CCC.CN([CH:23]=[O:24])C.O>C1COCC1.CCCCCC>[CH:10]1([CH2:9][O:8][C:5]2[CH:4]=[CH:3][C:2]([CH:23]=[O:24])=[CH:7][N:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 21914412HCID 21914412, compoundHCID 178418339Butyllithium

Product 1

HCID 86033953HCID 86033953, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of Intermediate 28 (895 mg) in anhydrous THF (10 ml) was added dropwise with a 1.6 M solution of n-butyllithium in hexane (2.70 ml, Ald) over 5 minutes with cooling at −78° C. under argon gas atmosphere, and stirred for 20 minutes. This reaction mixture was added with dehydrated DMF (330 μl, WAKO) over 3 minutes, stirred for 30 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was added with water (10 ml), and extracted with ethyl acetate (30 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 29, 1.04 g).

Workup

  1. stirringstirred for 30 minutes
  2. temperaturewarmed to room temperature
  3. stirringfurther stirred for 1 hour
  4. extractionextracted with ethyl acetate (30 ml×3)
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-54ede4ed7d8b44539ac78c7e97efd00c
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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