Sodium Methoxide → HCID 46228963, compound

HRID 46194Notes

Reaction equation

HRID 46194 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[S:28][C:29]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)=[N:30][N:31]=3)[CH:20]=2)[O:7][C@H:6]1[CH2:37][O:38]C(=O)C)(=O)C.C[O-].[Na+].[H][H]>CO>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:37][OH:38])[O:7]2)=[CH:20][C:21]=1[CH2:26][C:27]1[S:28][C:29]([C:32]2[O:33][CH:34]=[CH:35][CH:36]=2)=[N:30][N:31]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 67287618(2S,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 46228963HCID 46228963, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (187 mg, 0.31 mmol) from Step 3 in methanol (10 mL) was added sodium methoxide (25 wt % in methanol, 1.0 mL). The reaction mixture was stirred at ambient temperature for 2 h. Amberlite® IR120 hydrogen form was then added to neutralize the reaction mixture. The resin was filtered off and the filtrate was concentrated in vacuo. Purification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient) provided the title compound (78 mg, 0.18 mmol, 58%) as a white solid.

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient)

Sources & evidence

ORD record
ord-10e748bdcade4cd696cad0c4bc1367a9
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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