Oxygen → HCID 86728111, compound

HRID 627642Notes

Reaction equation

HRID 627642 reaction equation
[CH2:1]([CH:4]1[C@@:9]([CH2:20][F:21])([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[F:19])[N:8]=[C:7]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:6]([CH3:38])([CH3:37])[S:5]1(=[O:40])=[O:39])[CH:2]=[CH2:3].C(=O)(O)[O-:42].[Na+].O=O.[BH4-].[Na+]>C(Cl)Cl.CO>[C:25]([O:24][C:23]([N:22]([C:7]1[C:6]([CH3:38])([CH3:37])[S:5](=[O:39])(=[O:40])[CH:4]([CH2:1][CH2:2][CH2:3][OH:42])[C@@:9]([CH2:20][F:21])([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[F:19])[N:8]=1)[C:30](=[O:31])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 977OxygenHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86728109HCID 86728109, compound

Product 1

HCID 86728111HCID 86728111, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of tert-butyl N-[(3S)-2-allyl-3-(fluoromethyl)-3-(2-fluoro-5-nitro-phenyl)-6,6-dimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]-N-tert-butoxycarbonyl-carbamate (1.95 g, 3.33 mmol) in DCM (60 mL) and MeOH (20 mL) was added sodium bicarbonate (0.56 g, 6.65 mmol). The reaction mixture was cooled to −78° C. and ozonolized for about 15 min or until analysis showed no starting material present. A stream of oxygen was passed through the solution for 5 min, and then solid sodium borohydride (252 mg, 6.65 mmol) was added to the mixture. The flask was removed from the bath and allowed to reach RT and stirred for 1 h. The reaction was quenched with satd. aqueous NH4Cl, diluted with water to dissolve solids, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl N-tert-butoxycarbonyl-N-[(3S)-3-(fluoromethyl)-3-(2-fluoro-5-nitro-phenyl)-2-(3-hydroxypropyl)-6,6-dimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate which was taken to next step without further purification. LC/MS (ESI+) m/z=614 (M+Na).

Workup

  1. customThe flask was removed from the bath
  2. customto reach RT
  3. customThe reaction was quenched with satd
  4. additionaqueous NH4Cl, diluted with water
  5. dissolutionto dissolve solids
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8823c89b0fd84f25b8459bbdf13fc10b
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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