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

HRID 1736325노트

반응식

HRID 1736325 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-80a7a94ab31c4136ac61727147e92318
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541168

반응 노트

불러오는 중…