Ethanol → HCID 178463401, 화합물

HRID 335501

반응식

HRID 335501 반응식
[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]

참가 물질

8

반응물 4

HCID 702EthanolHCID 6386tert-ButanolHCID 920983-Hydroxy-3-phenyl-1-butyneHCID 66550531HCID 66550531, 화합물

생성물 1

HCID 178463401HCID 178463401, 화합물수율 21%

시약·촉매·용매 3

HCID 23978Copper촉매HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ca6b8f8ea5c4d049edeed19d56a9674
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884023B2

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