3-Octene → 2-Benzhydryloxycarbonyl-3-methyl-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 1660393Notes

Reaction equation

HRID 1660393 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]([C:19]1[N:20]2[CH:23]([S:24][CH2:25][C:26]=1[CH3:27])[CH:22]([NH:28][C:29]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:21]2=[O:48])([OH:18])=[O:17].CCC=CCCCC>C(#N)C>[CH:7]([O:17][C:16]([C:19]1[N:20]2[CH:23]([S:24][CH2:25][C:26]=1[CH3:27])[CH:22]([NH:28][C:29]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:21]2=[O:48])=[O:18])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 329353-OcteneHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 205148112-Carboxy-3-methyl-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

Product 1

HCID 202811642-Benzhydryloxycarbonyl-3-methyl-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-eneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of diphenyldiazomethane (12.3 g) in acetonitrile (200 cc) is added, in the course of 15 minutes, to a suspension of a mixture (28.8 g) of 2-carboxy-3-methyl-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (40%) and its oct-3-ene isomer (60%) in acetonitrile (500 cc), and the reaction mixture is then stirred for 2 hours at 25° C. The solvent is evaporated under reduced pressure (40 mm Hg) at 30° C. and the oily residue is redissolved in ethyl acetate (500 cc). The solution is washed successively with normal hydrochloric acid (until colourless), with a saturated sodium bicarbonate solution (3×100 cc), with water (100 cc) and with a saturated sodium chloride solution (100 cc), and is then dried and concentrated to dryness, to give a mixture (35.4 g) of 2-benzhydryloxycarbonyl-3-methyl-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (40%) and its oct-3-ene isomer (60%), in the form of a cream-coloured froth.

Workup

  1. customThe solvent is evaporated under reduced pressure (40 mm Hg) at 30° C.
  2. dissolutionthe oily residue is redissolved in ethyl acetate (500 cc)
  3. washThe solution is washed successively with normal hydrochloric acid (until colourless), with a saturated sodium bicarbonate solution (3×100 cc), with water (100 cc) and with a saturated sodium chloride solution (100 cc)
  4. customis then dried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9b75730dd41b48d5b7eca5d99d2a7386
Source dataset
uspto-grants-1981_12
Patent number
US04307230

Reaction notes

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