Acetonitrile → HCID 68431865, compound

HRID 1160202Notes

Reaction equation

HRID 1160202 reaction equation
BrC[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:5][CH:4]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[C:28](#N)C>C(OCC)(=O)C>[N:22]1([CH2:28][CH:7]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:10][C:9]2=[O:19])[C:6]2[CH:5]=[CH:4][CH:3]=[CH:21][CH:20]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8083MorpholineHCID 24963437HCID 24963437, compound

Product 1

HCID 68431865HCID 68431865, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-bromomethyl-benzyl)-5-(R)-phenyl-oxazolidin-2-one (30 mg, 0.086 mmol) and morpholine (0.038 mL, 0.433 mmol) in acetonitrile (2 mL) was heated at 70° C. for 4 hours. The reaction mixture was diluted with ethyl acetate (6 mL), washed with water (4 mL), brine (4 mL), dried over anhydrous sodium sulfate and concentrated to get the product. It was purified by chromatography on silica gel, eluting with 30-60% ethyl acetate in hexanes, to yield the title compound as a white solid (21 mg, 69%).

Workup

  1. washwashed with water (4 mL), brine (4 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto get the product
  5. customIt was purified by chromatography on silica gel
  6. washeluting with 30-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d78908ec12db486e8fdd4830f5af6232
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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