Ethanol → HCID 178463401、化合物

HRID 335501

反応式

HRID 335501 の反応式
[N:1]([CH2:4][C@H:5]1[O:13][C@H:12]2[C@H:8]([N:9]=[C:10]([NH:14][CH2:15][CH3:16])[S:11]2)[C@@H:7]([OH:17])[C@@H:6]1[OH:18])=[N+:2]=[N-:3].C(O)C.CC(O)(C)C.[C:27]1([C:33]([OH:37])([C:35]#[CH:36])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O.[Cu].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:15]([NH:14][C:10]1[S:11][CH:12]2[O:13][CH:5]([CH2:4][N:1]3[CH:36]=[C:35]([C:33]([OH:37])([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH3:34])[N:3]=[N:2]3)[CH:6]([OH:18])[CH:7]([OH:17])[CH:8]2[N:9]=1)[CH3:16]

参加物

8

反応物 4

HCID 702EthanolHCID 6386tert-ButanolHCID 920983-Hydroxy-3-phenyl-1-butyneHCID 66550531HCID 66550531、化合物

生成物 1

HCID 178463401HCID 178463401、化合物収率 21%

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒2 回

実験手順

In a 10 mL rb flask was added (3aR,5R,6S,7R,7aR)-5-(azidomethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (40 mg, 0.15 mmol, 1.00 eq.), copper turnings (66 mg; 1.05 mmol; 7.00 eq.) and copper(II)sulfate pentahydrate (7.5 mg; 0.03 mmol; 0.20 eq.). The flask was evacuated and filled with nitrogen. This procedure was repeated twice before ethanol (0.5 ml)/water (0.7 ml)/2-methylpropan-2-ol (1.3 ml) and 2-phenylbut-3-yn-2-ol (22 mg; 0.45 mmol; 3.00 eq.) was added into the mixture and stirred for 24 h to get the reaction completed. Product formation was confirmed by LCMS. The solution was diluted with 2 mL H2O, dried and separated with mass based prep HPLC to afford the desired product.

後処理

  1. customThe flask was evacuated
  2. additionfilled with nitrogen
  3. additionwas added into the mixture
  4. customto get the reaction
  5. customdried
  6. customseparated with mass

出典と根拠

ORDレコード
ord-1ca6b8f8ea5c4d049edeed19d56a9674
出典データセット
uspto-grants-2014_11
特許番号
US08884023B2

関連ノート

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