Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 10891697, compound

HRID 626939Notes

Reaction equation

HRID 626939 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]1([CH:31]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:32]2[CH2:35][C:34](=O)[CH2:33]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[C:25]1([CH:31]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:32]2[CH2:35][C:34](=[CH:20][C:21]([O:23][CH3:24])=[O:22])[CH2:33]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 37355581-(Diphenylmethyl)azetidin-3-one

Product 1

HCID 10891697HCID 10891697, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (triphenylphosphoranylidene)acetate (2.77 g, 8.29 mmol) was added to a mixture of 1-(diphenylmethyl)azetidin-3-one (1.64 g, 6.91 mmol) in THF (24 mL) and the resultant mixture was left to stir overnight. The mixture was concentrated under vacuum, then the residue was dissolved in hot 1:4 EtOAc/heptane (40 mL) and allowed to cool to room temperature. The resultant solid was filtered off and the filtrate was concentrated under vacuum. The crude residue was purified by FCC, eluting with 20% EtOAc in heptane, to afford the title compound (917 mg, 44%) as a pale yellow solid. Method B HPLC-MS: MH+ m/z 294, RT 1.43 minutes.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in hot 1:4 EtOAc/heptane (40 mL)
  3. filtrationThe resultant solid was filtered off
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude residue was purified by FCC
  6. washeluting with 20% EtOAc in heptane

Sources & evidence

ORD record
ord-f17dfe7c48a5460b855d82cb9c443c00
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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