Sodium Bicarbonate → HCID 86728106, compound

HRID 627631Notes

Reaction equation

HRID 627631 reaction equation
[CH2:1]([C@@H:4]1[C@:12]([C:14]2[C:15]([F:21])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=2)([CH3:13])[N:11]=[C:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:6]2([CH2:9][CH2:8][CH2:7]2)[S:5]1(=[O:31])=[O:30])[CH:2]=C.C(=O)(O)[O-:33].[Na+].[BH4-].[Na+]>C(Cl)Cl.CO>[Br:20][C:18]1[CH:19]=[C:14]([C@@:12]2([CH3:13])[N:11]=[C:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:6]3([CH2:9][CH2:8][CH2:7]3)[S:5](=[O:31])(=[O:30])[C@@H:4]2[CH2:1][CH2:2][OH:33])[C:15]([F:21])=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86728105HCID 86728105, compound

Product 1

HCID 86728106HCID 86728106, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((6R,7R)-6-allyl-7-(5-bromo-2-fluoropyridin-3-yl)-7-methyl-5,5-dioxido-5-thia-8-azaspiro[3.5]non-8-en-9-yl)carbamate (2.0 g, 3.87 mmol) in DCM (40 mL) and MeOH (10 mL) was added sodium bicarbonate (0.651 g, 7.75 mmol) and the resulting mixture was brought to −78° C. To this mixture was bubbled O3 for 15 min until the starting material was consumed. A stream of oxygen was passed through the solution for 5 min, then solid sodium borohydride (0.293 g, 7.75 mmol) was added to the mixture. The flask was removed from the bath and allowed to reach rt and stirred for 30 min. The mixture was carefully quenched with saturated NH4Cl, water was added and extracted with DCM. The combined organics were dried over Na2SO4, filtered, and concentrated to afford a white solid as tert-butyl ((6R,7R)-7-(5-bromo-2-fluoropyridin-3-yl)-6-(2-hydroxyethyl)-7-methyl-5,5-dioxido-5-thia-8-azaspiro[3.5]non-8-en-9-yl)carbamate (2.035 g, 3.91 mmol, 101% yield). LC/MS (ESI+) m/z=541.8 (M+H).

Workup

  1. customwas brought to −78° C
  2. customTo this mixture was bubbled O3 for 15 min until the starting material
  3. customwas consumed
  4. customThe flask was removed from the bath
  5. customto reach rt
  6. customThe mixture was carefully quenched with saturated NH4Cl, water
  7. additionwas added
  8. extractionextracted with DCM
  9. dry with materialThe combined organics were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-3b6207cc6e2b46cf925dee4116194e92
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…