Ammonium Chloride → HCID 59131023, compound

HRID 1992673Notes

Reaction equation

HRID 1992673 reaction equation
C([Li])CCC.[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O:25][C:26](=O)/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[F:36])OC(C)(C)C.[Cl-].[NH4+]>O1CCCC1.COC(C)(C)C.C1CCCCC1.O>[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:26](=[O:25])/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=1[F:36])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 59130989HCID 59130989, compoundHCID 178418339Butyllithium

Product 1

HCID 59131023HCID 59131023, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5M in hexanes) (100 mL, 250 mmol) was added dropwise to a stirred solution of (S)-(−)-4-benzyl-2-oxazolidinone (43.55 g, 250 mmol) in anhydrous tetrahydrofuran (350 mL) at 0° C. The resulting solution was cooled to −78° C. for 30 minutes and added dropwise to a stirring solution of tert-butyl (2E)-3-(2,4-difluorophenyl)prop-2-enoyl carbonate, from preparation 27 via cannula at −78° C. The resulting suspension was allowed to warm to 0° C. and saturated ammonium chloride solution (75 mL) was added, followed by water (50 mL). The phases were separated and the aqueous layer was extracted with ethyl acetate (2×300 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to give a slurry. Cyclohexane (178.5 mL) and tert-butyl methyl ether (126 mL) were added to the slurry and the mixture was stirred for 2 hours at room temperature. The resulting white solid was collected via filtration and dried in a vacuum oven at 40° C. to give the desired product, 45.48 g (61%).

Workup

  1. temperatureto warm to 0° C.
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×300 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a slurry
  8. filtrationThe resulting white solid was collected via filtration
  9. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-7716e6d52e3444e2b8460c8f59ac952c
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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