Iodine chloride → 4-(beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

HRID 19836

반응식

HRID 19836 반응식
[I:1]Cl.[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Si](C)(C)C)=[CH:26][CH:25]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]>ClCCl>[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([I:1])=[CH:26][CH:25]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]

참가 물질

4

반응물 2

HCID 24640Iodine chlorideHCID 866162484-(beta-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile

생성물 1

HCID 866162474-(beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A 1 M solution of iodine monochloride in dichloromethane (0.9 mL) is added to 4-(β-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile (0.26 g) dissolved in dichloromethane (5 mL). The solution is stirred at room temperature for 1 h and then quenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

후처리

  1. customquenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

출처 및 근거

ORD 기록
ord-d83fc3a51b5d4624b21202190cf07664
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745414B2

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