Sodium Carbonate → 5-[2-benzyloxy-4-((E)-hex-1-enyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660712노트

반응식

HRID 660712 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24](/B(O)O)=[CH:25]\[CH2:26][CH2:27][CH2:28][CH3:29].C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:24]=[CH:25]/[CH2:26][CH2:27][CH2:28][CH3:29])[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 5326225B-(1E)-1-Hexenylboronic acidHCID 688386435-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

생성물 1

HCID 688392905-[2-benzyloxy-4-((E)-hex-1-enyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
110 °C

실험 절차

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (200 mg, 0.45 mmol), trans-1-hexen-1-ylboronic acid (77 mg, 0.676 mmol), resin-bound PPh3Pd (692 mg, loading 0.13 mmol/g) and aqueous Na2CO3 (0.9 mL of a 2M solution) in DME (3 mL) is placed in a microwave vial and heated at 110° C. for 30 min. The mixture is filtered, diluted with EtOAc and washed with 1N HCl. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is purified by preparative HPLC to give the title compound.

후처리

  1. filtrationThe mixture is filtered
  2. additiondiluted with EtOAc
  3. washwashed with 1N HCl
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe residue is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-105f284162aa4b98b7266577f6f8db05
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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