Carbon Dioxide → HCID 123531982, compound

HRID 1481629Notes

Reaction equation

HRID 1481629 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:16]2)[C@@H:12]([F:28])[C:11]1=[O:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C(=O)=O>CO>[Si:1]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[S:16]2)[C@@H:12]([F:28])[C@H:11]1[OH:29])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 4311764Sodium borohydrideHCID 123671551HCID 123671551, compound

Product 1

HCID 123531982HCID 123531982, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl ((3aR,5R,7R,7aR)-5-(((tert-butyldimethylsilyl)oxy)methyl)-7-fluoro-6-oxo-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (2.57 g, 5.72 mmol) in dry MeOH (50 mL), at 0° C., was added NaBH4 (0.295 g, 7.80 mmol). After the mixture was stirred at 0° C. for 20 min a chip of dry ice was added, and the solvent was evaporated. The residue was dissolved in DCM (50 mL) and washed with satd. aqueous NaHCO3 (50 mL). The organic layer was collected, and the aqueous was extracted with DCM (2×30 mL). The combined extract was dried over anhydrous Na2SO4. After filtration the solvent was evaporated under reduced pressure, and the residue was purified on silica gel by flash column chromatography (EtOAc/hexanes, 1:10 to 1:3), affording tert-butyl ((3aR,5R,6S,7R,7aR)-5-(((tert-butyldimethylsilyl)oxy)methyl)-7-fluoro-6-hydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.95 g, 37%), as a sticky oil. 1H NMR (400 MHz, CDCl3) δ 6.11 (d, J=6.7 Hz, 1H), 4.84 (ddd, J=3.2, 6.7, 48.2 Hz, 1H), 4.45 (td, J=6.7, 16.6 Hz, 1H), 4.32-4.29 (m, 1H), 4.00-3.93 (m, 2H), 3.90-3.86 (m, 1H), 3.36 (s, 3H), 3.19 (s, br., 1H, (OH)), 1.53 (s, 9H), 0.90 (s, 9H), 0.093 (s, 3H), 0.087 (s, 3H).

Workup

  1. additionwas added
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM (50 mL)
  4. washwashed with satd
  5. customThe organic layer was collected
  6. extractionthe aqueous was extracted with DCM (2×30 mL)
  7. extractionThe combined extract
  8. dry with materialwas dried over anhydrous Na2SO4
  9. filtrationAfter filtration the solvent
  10. customwas evaporated under reduced pressure
  11. customthe residue was purified on silica gel by flash column chromatography (EtOAc/hexanes, 1:10 to 1:3)

Sources & evidence

ORD record
ord-7b8eecd0cf804a0bb31f4fb7f096b15f
Source dataset
uspto-grants-2016_08
Patent number
US09409924B2

Reaction notes

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