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

HRID 1736325Notes

Reaction equation

HRID 1736325 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-80a7a94ab31c4136ac61727147e92318
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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