p-Toluenesulfonic acid → cis-2-Azidomethyl-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine

HRID 2050397Notes

Reaction equation

HRID 2050397 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2[N:10]([C@H:21]3[C:24](=[O:25])[NH:23][C@H:22]3[C:26](OC)=O)[C:11](=[O:20])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.OCC1CCN1.CC1C=CC(S(O)(=O)=O)=CC=1.[N-:47]=[N+:48]=[N-:49].[Na+]>>[N:47]([CH2:26][C@H:22]1[C@@H:21]([N:10]2[C:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:11]2=[O:20])[C:24](=[O:25])[NH:23]1)=[N+:48]=[N-:49]

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 15251628(Azetidin-2-yl)methanolHCID 70577957Methyl cis-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine-2-carboxylate

Product 1

HCID 86736960cis-2-Azidomethyl-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine

Procedure

Sodium borohydride reduction of methyl cis-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine-2-carboxylate as described in Preparation 3, followed by conversion of the 2-hydroxymethylazetidine product to the p-toluenesulfonate derivative and reaction of this derivative with sodium azide as described in Preparation 4 gives the title compound.

Workup

  1. customas described in Preparation 4

Sources & evidence

ORD record
ord-39bb3bf4db0840dab8da4207cb6d4790
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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