Ozone → HCID 86728124, compound

HRID 627655Notes

Reaction equation

HRID 627655 reaction equation
[CH2:1]([C:4]1([CH3:40])[S:9](=[O:11])(=[O:10])[C:8]([CH3:13])([CH3:12])[C:7]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:6][C@@:5]1([C:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=1[F:39])[CH3:29])[CH:2]=C.C(=O)(O)[O-:42].[Na+].O=[O+][O-].[BH4-].[Na+]>C(Cl)Cl.CO.C(=O)=O.CC(C)=O.O=O>[C:17]([O:16][C:15]([N:14]([C:7]1[C:8]([CH3:13])([CH3:12])[S:9](=[O:11])(=[O:10])[C:4]([CH2:1][CH2:2][OH:42])([CH3:40])[C@:5]([C:30]2[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[CH:33]=[CH:32][C:31]=2[F:39])([CH3:29])[N:6]=1)[C:22](=[O:23])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])([CH3:19])([CH3:18])[CH3:20]

Participants

9

Reactant 4

HCID 24823OzoneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86728123HCID 86728123, compound

Product 1

HCID 86728124HCID 86728124, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 977OxygenSolventHCID 6344DichloromethaneSolventHCID 18522661Acetone cardiceSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl N-[(5R)-6-allyl-5-(2-fluoro-5-nitro-phenyl)-2,2,5,6-tetramethyl-1,1-dioxo-1,4-thiazin-3-yl]-N-tert-butoxycarbonyl-carbamate (0.18 g, 0.31 mmol) in DCM (2.4 ml) and MeOH (0.8 ml) was added sodium bicarbonate (0.053 g, 0.63 mmol) and then cooled in dry ice-acetone bath. A mixture of O3 in oxygen gas was bubbled through the solution until the blue color persisted. The excess ozone was removed by bubbling through oxygen gas for 5 minutes. Sodium borohydride (0.018 g, 0.47 mmol) was added and the mixture was stirred and allowed to warm to 0° C. After 30 minutes, the reaction was quenched by sat.NH4Cl and extracted with DCM. The combined extracts were washed with brine, dried and concentrated to give crude tert-butyl N-tert-butoxycarbonyl-N-[(5R)-5-(2-fluoro-5-nitro-phenyl)-6-(2-hydroxyethyl)-2,2,5,6-tetramethyl-1,1-dioxo-1,4-thiazin-3-yl]carbamate as a white solid. m/z (ESI) 611.0 (M+Na)+.

Workup

  1. customwas bubbled through the solution until the blue color
  2. customThe excess ozone was removed
  3. customby bubbling through oxygen gas for 5 minutes
  4. customthe reaction was quenched
  5. extractionNH4Cl and extracted with DCM
  6. washThe combined extracts were washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3d24a4e8acfc42c5adb5656e7368a245
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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