Phosphate → 2-(Dibenzyloxyphosphinyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1736325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736325
[Cs].[P:2]([O-:20])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].P([O-])([O-])([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:33][N:34]1[C:38](=[O:39])[CH:37]([CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[N:36]([CH3:45])[S:35]1(=[O:47])=[O:46]>CO>[CH2:13]([O:12][P:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O:20][CH2:33][N:34]1[C:38](=[O:39])[CH:37]([CH2:40][CH2:41][CH:42]([CH3:43])[CH3:44])[N:36]([CH3:45])[S:35]1(=[O:46])=[O:47])=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 5

HCID 1061PhosphateHCID 10796Cesium carbonateHCID 4193600DibenzylphosphateHCID 5354618CesiumHCID 15817425HCID 15817425, Verbindung

Produkt 1

HCID 99579892-(Dibenzyloxyphosphinyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To the cesium salt of dibenzyl phosphate (Formula III: A=B=CH2Ph) (prepared from 2.07 g of the phosphate and 1.21 g of cesium carbonate in methanol followed by removal of the methanol) in 30 ml of DMF was added 2-chloromethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 3.72 mmol) and the mixture was allowed to stir at room temperature for 48 hours. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was washed with water, brine and dried. The solvent was concentrated in vacuo and the residue purified by silica gel flash chromatography (60% ethyl acetate/hexane) to afford 0.29 g (15%) of 2-(dibenzyloxyphosphinyloxymethyl)-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3 ; A=B=CH2Ph) as an oil.

Aufarbeitung

  1. customfollowed by removal of the methanol) in 30 ml of DMF
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water, brine
  4. customdried
  5. concentrationThe solvent was concentrated in vacuo
  6. customthe residue purified by silica gel flash chromatography (60% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-80a7a94ab31c4136ac61727147e92318
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541168

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