Ethanol → (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-[(4-pyridin-2-yltriazol-1-yl)methyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

HRID 335489Notes

Reaction equation

HRID 335489 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.[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)#[CH:23]>[Cu].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O.CC(O)(C)C>[CH2:15]([NH:14][C:10]1[S:11][C@H:12]2[O:13][C@H:5]([CH2:4][N:1]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[N:3]=[N:2]3)[C@@H:6]([OH:18])[C@H:7]([OH:17])[C@H:8]2[N:9]=1)[CH3:16]

Participants

8

Reactant 3

HCID 702EthanolHCID 137268EthynylpyridineHCID 66550531CID 66550531

Product 1

HCID 178463442(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-[(4-pyridin-2-yltriazol-1-yl)methyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diolYield 25.5%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

In a 5 mL seal vial equipped with a stir bar, a septum 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 (40.00 mg; 0.15 mmol; 1.00 eq.), copper Not supported by ACD (65.10 mg; 1.02 mmol; 7.00 eq.) and copper (2+) sulfate pentahydrate (7.31 mg; 0.03 mmol; 0.20 eq.). The vial was evacuated and filled with N2. This procedure was repeated for twice before ethanol (0.40 ml)/water (0.60 ml)/2-methylpropan-2-ol (1.00 ml) and 2-ethynylpyridine (0.03 ml; 0.29 mmol; 2.00 eq.) was added into the mixture. The mixture was stirred at room temperature for overnight before 3 mL H2O was added into the mixture and dried via lyophilization. The mixture was purified with Yamazen C1 acidic condition affording 14.4 mg (20.1%) of the title compound as a white solid (HPLC 99%, retention time=1.73 min) once lyophilized.

Workup

  1. customIn a 5 mL seal vial
  2. customequipped with a stir bar
  3. customThe vial was evacuated
  4. additionfilled with N2
  5. additionwas added into the mixture
  6. additionwas added into the mixture
  7. customdried via lyophilization
  8. customThe mixture was purified with Yamazen C1 acidic condition

Sources & evidence

ORD record
ord-74622ff6de5c450cb416fb212d82cd9b
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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