1-(Triphenylphosphoranylidene)acetone → (2S)-2-{4-[(5-methyl-1H-1,2,3-triazol-1-yl)methyl]-2-oxo-1-pyrrolidinyl}butanamide

HRID 900311Notes

Reaction equation

[N:1]([CH2:4][CH:5]1[CH2:9][N:8]([C@@H:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12])[C:7](=[O:16])[CH2:6]1)=[N+:2]=[N-:3].[C:17]1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=CC(C)=O)[CH:22]=CC=C[CH:18]=1>C1(C)C=CC=CC=1>[CH3:22][C:17]1[N:1]([CH2:4][CH:5]2[CH2:9][N:8]([C@@H:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12])[C:7](=[O:16])[CH2:6]2)[N:2]=[N:3][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 50 ml 3 necked flask, fitted with magnetic stirrer and reflux condenser under inert atmosphere, 1 g (4.44 mmoles, 1 eq) of (2S)-2-[4-(azidomethyl)-2-oxo-1-pyrrolidinyl]butanamide 32 is suspended in 20 ml of toluene. 1.55 g (4.88 mmoles, 1.1 eq) of 1-(triphenylphosphoranylidene)acetone are added, and the mixture is heated up to 80° C. for 24 hours. After cooling down, the mixture is concentrated to dryness and purified by Prep LC (1 kg SiO2, CH2Cl2/MeOH/NH4OH, 94.5:5:0.5). It is suspended in 15 ml of water and lyophilised to give 240 mg of pure 52 as a clear oil, 42%. 7.3.4. Synthesis of of (2S)-2-[4-(isothiocyanatomethyl)-2-oxo-1-pyrrolidinyl]butanamide 49

Workup

temperatureAfter cooling down
concentrationthe mixture is concentrated to dryness
custompurified by Prep LC (1 kg SiO2, CH2Cl2/MeOH/NH4OH, 94.5:5:0.5)

Sources & evidence

ORD record: ord-a4cc6246a0224a2d825abb0bdb92a210
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358276B2

Reaction notes

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