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

HRID 660712ノート

反応式

HRID 660712 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-105f284162aa4b98b7266577f6f8db05
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

反応ノート

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