Dimethyl Sulfide → HCID 13276954, compound

HRID 1284841Notes

Reaction equation

O=[O+][O-].[O:4]=O.[CH2:6]([C:13]1[O:19][C@@H:18]2[C@@H:15]([C:16](=[O:24])[N:17]2[CH:20]=C(C)C)[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CSC>ClCCl>[CH2:6]([C:13]1[O:19][C@@H:18]2[C@@H:15]([C:16](=[O:24])[N:17]2[CH:20]=[O:4])[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

An ozone-oxygen mixture was passed through a solution, cooled to -70° C., of 2.56 g (10 millimols) of (1S,5R)-3-benzyl-6-(2-methylprop-1-enyl)-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one (R. J. Stoodley et al., J. C. S. Perkin I 1974, 181) in 75 ml of anhydrous dichloromethane, until a blue coloration was obtained. Thereafter, flushing with nitrogen was carried out for 10 minutes, and 5.9 ml (80 millimols) of dimethyl sulphide were then added at -70° C. The mixture was stirred for 1 hour at 0° C. and for 1 hour at room temperature, and then evaporated down in vacuo. The residue was dissolved in dichloromethane, and the solution was washed with saturated NaHCO3 solution and water, and dried over MgSO4. After the solvent had been removed in vacuo, the residue was triturated with ether. 1.2 g (52%) of (1S,5R)-3-benzyl-6-formyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one were obtained as colorless crystals, melting point 90°-92° C.

Workup

customwas obtained
customThereafter, flushing with nitrogen
customevaporated down in vacuo
dissolutionThe residue was dissolved in dichloromethane
washthe solution was washed with saturated NaHCO3 solution and water
dry with materialdried over MgSO4
customAfter the solvent had been removed in vacuo
customthe residue was triturated with ether

Sources & evidence

ORD record: ord-4e4a1dff706e47309d3d2f12db3f4242
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04564473

Reaction notes

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