Dimethyl Sulfide → {1-[4-(8-Formyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037409Notes

Reaction equation

HRID 1037409 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22](C=C)[CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3C3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CSC>CO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19](=[O:20])[C:24]4[C:25](=[C:26]([CH:27]=[O:28])[CH:21]=[CH:22][CH:23]=4)[O:28][C:27]=3[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 1068Dimethyl SulfideHCID 68227664{1-[4-(4-oxo-2-phenyl-8-vinyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 86671056{1-[4-(8-Formyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of {1-[4-(4-oxo-2-phenyl-8-vinyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester in MeOH (1 mL) and DCM (4 mL) was cooled with stirring to −78° C. Ozone was bubbled through the reaction mixture for 75 min with stirring, followed by air for 5 min with stirring. Dimethylsulfide (0.027 ml, 0.366 mmol) was added and the resultant mixture was allowed to warm to RT and stirred for 2 h. The solvent was removed by bubbling nitrogen through the reaction mixture. The residue was dissolved in EtOAc and washed with brine. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a gum (81 mg, 90%). LCMS (Method G): RT=4.24 min, [M+H]+=496.

Workup

  1. customOzone was bubbled through the reaction mixture for 75 min
  2. stirringwith stirring
  3. stirringwith stirring
  4. temperatureto warm to RT
  5. stirringstirred for 2 h
  6. customThe solvent was removed
  7. customby bubbling nitrogen through the reaction mixture
  8. dissolutionThe residue was dissolved in EtOAc
  9. washwashed with brine
  10. dry with materialThe organic extracts were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09a7856e17dd439ea3cfca77e2d75590
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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