Ammonium Chloride → HCID 67232581, compound

HRID 2047459Notes

Reaction equation

HRID 2047459 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)=[N:13][CH:14]=1.C(Cl)(=O)C(C)(C)C.[Li].O1CCNC1=O.C([Li])CCC.[CH2:39]([C@@H:46]1[CH2:50][O:49][C:48](=[O:51])[NH:47]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[Cl-].[NH4+]>C1COCC1.C(N(CC)CC)C>[CH2:39]([C@@H:46]1[CH2:50][O:49][C:48](=[O:51])[N:47]1[C:17](=[O:19])/[CH:16]=[CH:15]/[C:12]1[CH:11]=[CH:10][C:9]([F:8])=[CH:14][N:13]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

9

Reactant 6

HCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 67231731HCID 67231731, compoundHCID 67232314HCID 67232314, compoundHCID 178418339Butyllithium

Product 1

HCID 67232581HCID 67232581, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (2.5 g) obtained in step 3 in THF (180 mL) were added at −78° C. pivaloyl chloride (12.9 g) and triethylamine (2.25 g) and the mixture was stirred for 2 hr. To this mixture was added at −78° C. a solution of oxazolidinone lithium anion (prepared by adding n-butyllithium (2.5M hexane solution, 5.34 mL) to (R)-4-benzyloxazolidin-2-one (1.73 g) in THF (180 mL) at −78° C. and stirring for 1 hr), and the mixture was stirred at room temperature for 18 hr. The reaction was discontinued by adding saturated aqueous ammonium chloride solution (200 mL), and the mixture was extracted with ethyl acetate (300 mL). The extract was dried, concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (25% ethyl acetate/hexane) to give (4R)-4-benzyl-3-[(2E)-3-(5-fluoropyridin-2-yl)prop-2-enoyl]-1,3-oxazolidin-2-one (2.3 g, 80%) as a pale-yellow oil.

Workup

  1. additionTo this mixture was added at −78° C.
  2. stirringthe mixture was stirred at room temperature for 18 hr
  3. extractionthe mixture was extracted with ethyl acetate (300 mL)
  4. customThe extract was dried
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c6c391cee3a8439da43a5bc9c9fd4086
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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