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Sodium Bicarbonate → 2-(2-Methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine

HRID 6774
ノート
印刷プレビュー

反応式

HRID 6774 の反応式
CC(C)(OC([N:7]1[CH2:12][CH2:11][N:10]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[N:15]=[C:9]2[CH:8]1[CH2:24][CH2:25][S:26][C:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:15]=[C:9]2[CH:8]([CH2:24][CH2:25][S:26][C:27]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:7][CH2:12][CH2:11][N:10]2[CH:13]=1
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 516892Sodium BicarbonateHCID 220168347-((1,1-Dimethylethoxy)carbonyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine

生成物 1

HCID 220168072-(2-Methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The product from Step 13.f. (2.50 g, 3.96 mmol) was dissolved in CH2Cl2 (16.0 ml) and treated with Tfa (4.0 ml) at room temperature under N2 for about 3.5 hours. The reaction was then poured cautiously into a saturated NaHCO3 solution (150 ml) and the product was extracted with CH2Cl2 (2×50 ml), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using 9:1/hexanes:EtOAc and then 100% EtOAc as eluants. Product fractions were combined and concentrated under reduced pressure to obtain a white foam (1.35 g, 64%) which was used without further purification. Mass spec. 532.4 MH+.

後処理

  1. additiontreated with Tfa (4.0 ml) at room temperature under N2 for about 3.5 hours
  2. extractionthe product was extracted with CH2Cl2 (2×50 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel using 9:1/hexanes
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bc0ba97610434c6a8c9e80143daf1a08
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07084135B1

反応ノート

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