HCID 86753539, compound → HCID 86753541, compound

HRID 342297Notes

Reaction equation

HRID 342297 reaction equation
[N+:1]([C:4]1[CH:63]=[CH:62][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([N:15]2[CH2:19][CH2:18][C@H:17]([S:20][C:21]([CH2:23][C@H:24]3[N:27]([C:28]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=4)=O)=C(C)C)[C:26](=[O:45])[C@@H:25]3[C@H:46]([O:48][C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=3)=[O:50])[CH3:47])=[O:22])[CH2:16]2)[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(Cl)Cl>[N+:1]([C:4]1[CH:63]=[CH:62][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([N:15]2[CH2:19][CH2:18][C@H:17]([S:20][C:21]([CH2:23][C@H:24]3[N:27]([CH2:28][CH2:32][O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=4)[C:26](=[O:45])[C@@H:25]3[C@H:46]([O:48][C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=3)=[O:50])[CH3:47])=[O:22])[CH2:16]2)[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 86753539HCID 86753539, compound

Product 1

HCID 86753541HCID 86753541, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

34 mg (0.038 mmole) of (3S, 4R)-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-3-ylthio]carbonylmethyl)-1-[2-methyl-1-(p-nitrobenzyloxycarbonyl)-prop-1-enyl]-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-azetidinone were dissolved in 10 ml of methylene chloride. Ozone was bubbled through the solution at -78° C. For 3 minutes. The mixture was then left to stand at that temperature for 10 minutes, after which nitrogen gas was bubbled through to drive out the excess ozone. 50 mg of dimethyl sulphide were then added to the mixture, which was then warmed to room temperature over about 10 minutes and poured into a mixture of ice and water. The chloroform layer was separated, washed with water and dried over anhydrous sodium sulphate. The solvent was distilled off, to afford 33 mg (yield 100%) of the title product as an oily substance.

Workup

  1. customOzone was bubbled through the solution at -78° C
  2. waitThe mixture was then left
  3. waitto stand at that temperature for 10 minutes
  4. customafter which nitrogen gas was bubbled through
  5. addition50 mg of dimethyl sulphide were then added to the mixture, which
  6. additionpoured into a mixture of ice and water
  7. customThe chloroform layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-fe404956a26e4fb181fd45f8dd3f9da9
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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