Triphenylphosphine → (3R)-3-(5-hexen-1-yl)-N-benzoxy-2-azetidinone

HRID 1786112Notes

Reaction equation

HRID 1786112 reaction equation
O[CH2:2][C@@H:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[C:4]([NH:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:15]([C@@H:3]1[CH2:2][N:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]1=[O:5])[CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86621280(2R)-2-(hydroxymethyl)-N-benzoxy-7-octenamide

Product 1

HCID 68849452(3R)-3-(5-hexen-1-yl)-N-benzoxy-2-azetidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (2R)-2-(hydroxymethyl)-N-benzoxy-7-octenamide (1.51 g, 5.47 mmol) and triphenylphosphine (1.72 g, 6.56 mmol) in THF (50 mL) was added dropwise diisopropyl azodicarboxylate (1.3 mL, 6.56 mmol) at 0° C. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction was then quenched with water (50 mL). The aqueous layer was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine, and dried over MgSO4. After removing the solvent under vacuum, the residue was purified by flash column chromatography (hexane:EtOAc 6/1) to provide the title compound. MH+260.

Workup

  1. customThe reaction was then quenched with water (50 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent under vacuum
  6. customthe residue was purified by flash column chromatography (hexane:EtOAc 6/1)

Sources & evidence

ORD record
ord-c05e08bc207e426bbf7d1ad083546fd2
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

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