Dimethyl Sulfide → HCID 118036964, compound

HRID 1778017Notes

Reaction equation

HRID 1778017 reaction equation
[O:1]=[O+][O-].[CH:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]=2[N:23]=1)=C.CSC>C(Cl)Cl.O>[CH:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]=2[N:23]=1)=[O:1]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 118036474HCID 118036474, compound2×

Product 1

HCID 118036964HCID 118036964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone was bubbled through a mixture of tert-butyl 2-vinyl-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxylate (intermediate 239, 470 mg, 1.66 mmol) in DCM (6.5 ml) at −78° C. After 15 minutes, the intermediate ozonide was treated with dimethyl sulfide (0.86 ml, 11.62 mmol) and then the reaction mixture was slowly warmed to room temperature. After 1.5 h, the mixture was diluted with H2O and extracted with DCM (3×). The combined organic layers were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and evaporated to give the crude title compound as a light brown solid. (UPLC-MS 6) tR 1.04; ESI-MS 277.1 [M+H]+.

Workup

  1. waitAfter 1.5 h
  2. extractionextracted with DCM (3×)
  3. washThe combined organic layers were washed with sat. aq. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b8f5eb211bc84e6e83e18e510961ec99
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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