Ozone → HCID 18925200, compound

HRID 1289226Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([N:12]([CH:16]2[C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][C:19]=3[CH2:18][CH2:17]2)[N:26]=[C:25]([CH3:29])[N:24]([CH2:30][O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[C:23]4=[O:38])[CH2:13][C:14]#[CH:15])[CH:9]=[CH:8][C:3]=1[CH:4]=C(C)C.[O:39]=[O+][O-]>C(Cl)Cl.C(O)C>[F:1][C:2]1[CH:11]=[C:10]([N:12]([CH:16]2[C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][C:19]=3[CH2:18][CH2:17]2)[N:26]=[C:25]([CH3:29])[N:24]([CH2:30][O:31][C:32](=[O:37])[C:33]([CH3:35])([CH3:36])[CH3:34])[C:23]4=[O:38])[CH2:13][C:14]#[CH:15])[CH:9]=[CH:8][C:3]=1[CH:4]=[O:39]

Participants

Conditions

Temperature: -70 °C

Procedure

o-Fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]-β,β-dimethylstyrene (0.626 g) was dissolved in a mixture of methylene chloride (2 ml) and ethanol (250 ml). The mixture was cooled to -70° C. and ozone gas was passed into the solution for 7.5 minutes. Argon gas was bubbled into the solution for 5 minutes. Dimethyl sulphide (4 ml) was added and the mixture was allowed to warm to ambient temperature. The mixture was evaporated and the residue was purified by column chromatography using a 1:1 mixture of hexane and ethyl acetate as eluant. There was thus obtained o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzaldehyde (0.47 g);

Workup

customArgon gas was bubbled into the solution for 5 minutes
additionDimethyl sulphide (4 ml) was added
temperatureto warm to ambient temperature
customThe mixture was evaporated
customthe residue was purified by column chromatography
additiona 1:1 mixture of hexane and ethyl acetate as eluant

Sources & evidence

ORD record: ord-aea69b1f65874122a60ab3525fea9cff
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747499

Reaction notes

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