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

HRID 1736325ノート

反応式

HRID 1736325 の反応式
[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

参加物

7

反応物 5

HCID 1061PhosphateHCID 10796Cesium carbonateHCID 4193600DibenzylphosphateHCID 5354618CesiumHCID 15817425HCID 15817425、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-80a7a94ab31c4136ac61727147e92318
出典データセット
uspto-grants-1996_07
特許番号
US05541168

反応ノート

読み込み中…