HCID 86717461, compound → (2ξ)-2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-hexitol

HRID 712114Notes

Reaction equation

HRID 712114 reaction equation
C([O:4][CH2:5][CH:6]1[CH:11]=[CH:10][C@H:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][O:7]1)(=O)C>[Pd].CO>[OH:4][CH2:5][CH:6]1[O:7][CH2:8][C@@H:9]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 86717461HCID 86717461, compound

Product 1

HCID 86717565(2ξ)-2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-hexitolYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{(5S)-5-[(tert-Butoxycarbonyl)amino]-5,6-dihydro-2H-pyran-2-yl}methyl acetate (from example 19, step 5) (3.47 g, 12.8 mmol) and 10% palladium on carbon (1.4 g) in methanol (60 mL) was stirred under a H2 balloon at room temperature for 2 h. The reaction mixture was filtered and the filtrate was treated with 1.0 M sodium hydroxide in water (12 mL). After stirring for 4 h, the reaction solution was concentrated and diluted with ethyl acetate. The organic layer was separated and washed with brine, dried over Na2SO4, and concentrated. The residue was purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (0.77 g, 26%). LCMS calculated for C6H14NO2 (M−100+H)+: m/z=132.1. Found: 132.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was treated with 1.0 M sodium hydroxide in water (12 mL)
  3. concentrationthe reaction solution was concentrated
  4. additiondiluted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified with prep-LCMS (XBridge C18 column
  10. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-62c2f1d031924dcb8b7b334d8a25209b
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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