Toluene-p-sulphonic anhydride → 2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonate

HRID 1011456노트

반응식

HRID 1011456 반응식
[N+:1]([C:4]1[N:5]([CH2:9][C:10]2[N:11]=[N:12][N:13]([CH2:15][CH2:16][OH:17])[CH:14]=2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[O:18](S(C1C=CC(C)=CC=1)(=O)=O)[S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=O)=[O:20]>C(Cl)Cl>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:17][CH2:16][CH2:15][N:13]2[CH:14]=[C:10]([CH2:9][N:5]3[CH:6]=[CH:7][N:8]=[C:4]3[N+:1]([O-:3])=[O:2])[N:11]=[N:12]2)(=[O:20])=[O:18])=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 77773Toluene-p-sulphonic anhydrideHCID 575402032-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol

생성물 1

HCID 595110572-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl 4-methylbenzenesulfonate수율 53.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a round bottom flask containing alcohol 11 (160 mg, 0.672 mmol), TEA (136 mg, 1.34 mmol) and DCM (5 mL) was added Ts2O (263 mg, 0.806 mmol). The reaction was stirred at RT for 4 hrs. TLC indicated that the reaction was complete. The reaction was concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 140 mg (53% yield) of 12 as a pale orange oil. Mass Spec (lo-res): Calc'd for C15H16N6O5S: 392.092; found: 393.10 (M+H).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified on a silica gel cartridge

출처 및 근거

ORD 기록
ord-20b5fae0eae44ddc852e1d66daddc2d0
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977361B2

반응 노트

불러오는 중…