Triphenylphosphine → HCID 67509560, compound

HRID 1400040Notes

Reaction equation

HRID 1400040 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][C@H:23]([CH2:25][N:26]=[N+]=[N-])[O:22][C:21]4=[O:29])=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:24][C@H:23]([CH2:25][NH2:26])[O:22][C:21]4=[O:29])=[CH:18][CH:19]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86667227HCID 86667227, compound2×

Product 1

HCID 67509560HCID 67509560, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[4-{5(R)-azidomethyl-2-oxo-oxazolidin-3-yl}-phenyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (Intermediate IV, Step 6) (750 mg, 1.95 mmol) and triphenylphosphine (700 mg, 2.1 mmol) in THF (30 mL) was stirred at r.t. for 6 h. Water (1.5 mL) was added and the reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was then diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with brine (100 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.5:9.5 MeOH:CHCl3) to provide the title compound (450 mg, 62%) as off white solid.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 12 h
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, 0.5:9.5 MeOH:CHCl3)

Sources & evidence

ORD record
ord-454d86f7fc5c4b3f89fe0fa0a9ff55a7
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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