Ozone → HCID 86747402, compound

HRID 258428Notes

Reaction equation

HRID 258428 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][S:11][C@H:12]1[N:15]([CH:16]([C:30]([CH3:32])=C)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:33])[C@H:13]1[NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[O:45]=[O+][O-]>CO.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][S:11][C@H:12]1[N:15]([C:16](=[C:30]([OH:45])[CH3:32])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:33])[C@H:13]1[NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 24823OzoneHCID 12912424HCID 12912424, compound

Product 1

HCID 86747402HCID 86747402, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 4-nitrobenzyl 2-[(3R,4R)-4[(benzothiazol-2-yl)dithio]-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methyl-3-butenoate (XIIIc. 1.52 g 0.00244 mole) in 2:1 methanol/dichloromethane (165 mL), at -78° C., was treated with a stream of dry ozone until a pale blue coloration was reached (10 min). Nitrogen was then bubbled through the solution to discharge the blue color and methyl sulfide (1.5 mL) was added. The solution allowed to reach 0° C. over the course of 2 h. Evaporation of the solvents gave a crude product which was purified by flash-chromatography over silica gel (65% ethyl acetate in hexane) to yield 1.448 g (95%) of the title compound, XIVb, as a white foam.

Workup

  1. custom(10 min)
  2. customNitrogen was then bubbled through the solution
  3. additionwas added
  4. customto reach 0° C. over the course of 2 h
  5. customEvaporation of the solvents
  6. customgave a crude product which
  7. customwas purified by flash-chromatography over silica gel (65% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2a3840db8ca14b07b4f20b7a9f401b77
Source dataset
uspto-grants-1993_11
Patent number
US05266691

Reaction notes

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