Ozone → HCID 71006902, compound

HRID 403354Notes

Reaction equation

HRID 403354 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:18]2[S:17][CH:16]=[N:15][C:14]=2/[C:13](=C/C(OC)=O)/[CH2:12][CH2:11][C@H:10]1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[F:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:32]=[O+][O-]>C(Cl)Cl>[F:31][C:25]1[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:24]=1[C@@H:10]1[CH2:11][CH2:12][C:13](=[O:32])[C:14]2[N:15]=[CH:16][S:17][C:18]=2[C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 24823OzoneHCID 70983307HCID 70983307, compound

Product 1

HCID 71006902HCID 71006902, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-methyl 2-((7S,8S)-8-(tert-butoxycarbonylamino)-7-(2,3-difluorophenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-4-ylidene)acetate (68 mg, 0.15 mmol) in methylene chloride (5 mL) was treated with ozone under −78° C. for 2 min. The reaction mixture was purged with nitrogen and quenched with dimethyl sulfide. The solvent was removed under vacuum and the product was purified by flash chromatography, eluting with ethyl acetate in hexane from 0 to 100% to afford the desired product (34.5 mg, 58%): 1H NMR (400 MHz, CHLOROFORM-d) δ 8.73 (s, 1H), 7.16-7.09 (m, 3H), 5.62-5.53 (m, 1H), 5.13-5.05 (m, 1H), 3.64-3.53 (m, 1H), 3.13-3.02 (m, 1H), 3.01-2.92 (m, 1H), 2.38-2.24 (m, 2H), 1.36-1.29 (m, 9H); 19F NMR (400 MHz, CHLOROFORM-d) δ −137.33, −141.96.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. customquenched with dimethyl sulfide
  3. customThe solvent was removed under vacuum
  4. customthe product was purified by flash chromatography
  5. washeluting with ethyl acetate in hexane from 0 to 100%

Sources & evidence

ORD record
ord-4f43ad39c7594274a01b62eb146d4c0a
Source dataset
uspto-grants-2014_06
Patent number
US08748429B2

Reaction notes

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