Bromoacetyl bromide → HCID 40562710, compound

HRID 629765Notes

Reaction equation

HRID 629765 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[Br:18][CH2:19][C:20](Br)=[O:21]>C1COCC1.C(=O)=O.CC(C)=O>[Br:18][CH2:19][C:20]([N:8]1[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10][C:9]1=[O:12])=[O:21]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 40562710HCID 40562710, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18522661Acetone cardiceSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (4R)-4-phenyl-1,3-oxazolidin-2-one (100 g, 613 mmol) in THF (2 L) under a nitrogen atmosphere was cooled to −78° C. in dry ice-acetone bath. To the stirred solution was added n-BuLi (337 mL, 2 M solution in cyclohexane, 675 mmol) dropwise over a period of 30 min, followed by the addition of 2-bromoacetyl bromide (123.7 g, 613 mmol) over 15 min. The resulting solution was stirred at 25° C. for 2 h. The reaction was quenched with aqueous NH4Cl (500 mL), and the mixture was extracted three times with EtOAc (3×1 L). The combined organic extracts were washed with water (500 mL) and brine (500 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give the title compound as a brown solid. The crude product was used directly in the next step.

Workup

  1. customThe reaction was quenched with aqueous NH4Cl (500 mL)
  2. extractionthe mixture was extracted three times with EtOAc (3×1 L)
  3. washThe combined organic extracts were washed with water (500 mL) and brine (500 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-37cdb8a0b6d24273b5162e730277bf67
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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