HCID 23322744, compound → HCID 23322757, compound

HRID 279838Notes

Reaction equation

HRID 279838 reaction equation
[N:1]([CH:4]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]([CH:13]([C:15]([O:17]C)=[O:16])[CH3:14])[C:5]1=[O:19])=[N+:2]=[N-:3]>[OH-].[Na+]>[N:1]([CH:4]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]([CH:13]([C:15]([OH:17])=[O:16])[CH3:14])[C:5]1=[O:19])=[N+:2]=[N-:3]

Participants

3

Reactant 1

HCID 23322744HCID 23322744, compound

Product 1

HCID 23322757HCID 23322757, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Add 170 mg of this azide to a suspension of 30 mg NaH in 3 ml THF followed by a solution of 400 mg methyl 2-iodoproprionate in 2 ml THF. Heat the reaction mixture under nitrogen at 55° for 18 hr. Cool the reaction and add a few drops of H2O followed by ether. Wash the mixture with 5% NaHSO3, water, and brine. Dry the organic phase and concentrate in vacuo. Chromatograph this crude product on silica gel eluting with ethyl acetatehexane and isolate 3-azido-1-(1-carbomethoxyethyl)- perhydroazonin-2-one. Hydrolyze this ester in 1M NaOH. Acidify the reaction and extract with methylene chloride to obtain 3-azido-1-(1-carboxyethyl)perhydroazonin-2-one. Separate the diastereomers by reverse phase chromatography using acetonitrile-water mixtures.

Workup

  1. customthe reaction
  2. extractionextract with methylene chloride

Sources & evidence

ORD record
ord-ab28ca95ef764d04afe739198cf9d2ed
Source dataset
uspto-grants-1986_05
Patent number
US04587238

Reaction notes

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