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Phosphorus sulfide (P2S5) → 3-[4-(2-Oxo-3-propyl-6-thioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

HRID 1793819
ノート
印刷プレビュー

反応式

HRID 1793819 の反応式
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20](=O)[NH:19][C:18](=[O:24])[N:17]([CH2:25][CH2:26][CH3:27])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20](=[S:30])[NH:19][C:18](=[O:24])[N:17]([CH2:25][CH2:26][CH3:27])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14817Phosphorus sulfide (P2S5)HCID 213520793-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

生成物 1

HCID 865856363-[4-(2-Oxo-3-propyl-6-thioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester収率 38.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester (250 mg, 0.64 mmol) was dissolved in 8 mL of pyridine. P4S10 (430 mg, 1.5 eq) was added and the reaction mixture was stirred under reflux for 3 h. It was then cooled to rt and quenched with 3 mL of H2O and then with enough 6 N HCl to bring the pH to 3. The resulting reaction mixture was extracted with CHCl3. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by preparative HPLC to afford 100 mg of the desired product.

後処理

  1. temperatureunder reflux for 3 h
  2. customquenched with 3 mL of H2O
  3. customThe resulting reaction mixture
  4. extractionwas extracted with CHCl3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-cfad80d178cc4a3c8612eeb4e41b17a8
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07022686B2

反応ノート

読み込み中…

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