Sodium Thiosulfate → HCID 86673866, compound

HRID 1527488Notes

Reaction equation

HRID 1527488 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=C)[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2].O.C[N+]1([O-])CC[O:25]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=[O:25])[CH:12]=[C:11]([Cl:17])[C:10]=1[F:18])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 68283690(3-Chloro-2-fluoro-5-vinyl-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 86673866HCID 86673866, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (3-chloro-2-fluoro-5-vinyl-benzyl)-carbamic acid tert-butyl ester (2.7 g, 9.5 mmol) in acetone (20 mL) was added N-methylmorpholine-N-oxide monohydrate (1.5 g, 11 mmol) and a solution of 4% aq. osmiumtetraoxide (3.7 mL, 0.5 mmol). The reaction was stirred for 1 h, saturated aqueous Na2S2O3-solution was added and stirring was continued for one hour. After extraction with EtOAc and removal of the solvent in vacuo, the residue was dissolved in acetone/water (3:1, 40 mL) and NalO4 (4.0 g, 19 mmol) was added. After stirring for 2 h at ambient temperature, the reaction mixture was filtered, washed with EtOAc, extracted with EtOAc, dried (Na2SO4) and the solvent was removed in vacuo to give the title compound which was used without further purification. tR (HPLC conditions c): 5.22 min.

Workup

  1. stirringstirring
  2. waitwas continued for one hour
  3. extractionAfter extraction
  4. customwith EtOAc and removal of the solvent in vacuo
  5. dissolutionthe residue was dissolved in acetone/water (3:1, 40 mL)
  6. additionNalO4 (4.0 g, 19 mmol) was added
  7. stirringAfter stirring for 2 h at ambient temperature
  8. filtrationthe reaction mixture was filtered
  9. washwashed with EtOAc
  10. extractionextracted with EtOAc
  11. dry with materialdried (Na2SO4)
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a3660d11c91c46a0b6574698e8a236d7
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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