Ethanol → HCID 178463401, compound

HRID 335501

Reaction equation

HRID 335501 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 178463401HCID 178463401, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1ca6b8f8ea5c4d049edeed19d56a9674
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Linked notes

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