p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoate → p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-4,4-dimethyl-5-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thio]-3-oxopentanoate

HRID 2371898Notes

Reaction equation

HRID 2371898 reaction equation
[C:1]([S:5][CH:6]1[N:9]([CH:10]([C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26]Cl)[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:31])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][N:33]1[C:37]([SH:38])=[N:36][N:35]=[N:34]1>CN(C)C=O>[C:1]([S:5][CH:6]1[N:9]([CH:10]([C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26][S:38][C:37]2[N:33]([CH3:32])[N:34]=[N:35][N:36]=2)[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:31])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14460305p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoateHCID 178482017HCID 178482017, compound

Product 1

HCID 14460321p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-4,4-dimethyl-5-[(1-methyl-1,2,3,4-tetrazol-5-yl)-thio]-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 118 mg (0.25 mmol) of p-nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoate and 82 mg (0.59 mmol) of the Na salt of 1-methyl-5-mercapto-1,2,3,4-tetrazole are stirred for 20 hours at room temperature in 0.2 ml of dimethylformamide. The reaction mixture is chromatographed directly on a chromatography column containing 6 g of silica gel using toluene:ethyl acetate (19:1), to give 60 mg of pure title compound as a non-crystalline solid.

Workup

  1. customThe reaction mixture is chromatographed directly on a chromatography column
  2. additioncontaining 6 g of silica gel

Sources & evidence

ORD record
ord-c506ed3bad57461d971533d3e5914477
Source dataset
uspto-grants-1992_03
Patent number
US05096899

Reaction notes

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