HCID 123292264, compound → HCID 123928181, compound

HRID 1481618Notes

Reaction equation

HRID 1481618 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]([OH:20])[CH3:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[S:14]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[C:18]([C@H:17]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[S:14]2)[CH2:10][C@@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:20])[CH3:19]

Participants

3

Reactant 1

HCID 123292264HCID 123292264, compound

Product 1

HCID 123928181HCID 123928181, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((3aR,5R,6S,7aR)-6-(benzyloxy)-5-(1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.406 g, 0.961 mmol) in dry DCM (20 mL) was added DMP (0.615 g, 1.45 mmol). The reaction mixture was stirred at room temperature for 3 h, and then concentrated. The residue was diluted with saturated aqueous NaHCO3 solution (20 mL) and 1 M Na2S2O3 aqueous solution (5 mL), and extracted with EtOAc (2×20 mL). The combined extract was dried over Na2SO4. After filtration the solvent was evaporated under reduced pressure, and the residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:4 to 2:3), affording tert-butyl ((3aR,5S,6S,7aR)-5-acetyl-6-(benzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.32 g), which was impure and used in the next step without further purification.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with saturated aqueous NaHCO3 solution (20 mL) and 1 M Na2S2O3 aqueous solution (5 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas evaporated under reduced pressure
  8. customthe residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:4 to 2:3)

Sources & evidence

ORD record
ord-c2b4a2845b21497b8503207227f134a5
Source dataset
uspto-grants-2016_08
Patent number
US09409924B2

Reaction notes

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