Triphenylphosphine → HCID 67065476, compound

HRID 2391955Notes

Reaction equation

HRID 2391955 reaction equation
[N:1]([CH:4]([C:9]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O.C1COCC1>[CH3:10][C:9]([CH3:17])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C@@H:4]([C:5]([O:7][CH3:8])=[O:6])[NH2:1]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 57826597HCID 57826597, compound

Product 1

HCID 67065476HCID 67065476, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-azido-3-methyl-3-phenylbutanoate (2.6 g, 11.2 mmol) and PPh3 (4.4 g, 16.7 mmol) in H2O (400 uL) and THF (100 mL) was stirred at 25° C. over 2 d then at 50° C. for 12 h. The solution was concentrated and purified via column chromatography (silica, 5% MeOH in DCM (1% NH4OH)) yielding the title compound (1.4 g, quant.): LCMS (ES) m/e 208 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified via column chromatography (silica, 5% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-8e301dd28f62410e951361a8e66727f1
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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