HCID 86736116, compound → HCID 131711103, compound

HRID 372260Notes

Reaction equation

HRID 372260 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][CH:10](OC)[O:11]C)=[N+:2]=[N-:3]>Cl.O1CCOCC1.O>[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][CH:10]=[O:11])=[N+:2]=[N-:3]

Participants

5

Reactant 1

HCID 86736116HCID 86736116, compound

Product 1

HCID 131711103HCID 131711103, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 500 mg (2.5 mmole) of cis-3-azido-2-(2,2-dimethoxyethyl)-4-oxoazetidine in 10 ml of 5% HCl and 10 ml of dioxane was stirred at 35° for 1/2 hour. The mixture was diluted with water and extracted with 50 ml of benzene. The aqueous phase was saturated with brine and extracted 10 times with 50 ml of ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and evaporated to dryness. The residue was titurated with ether to give the desired aldehyde, 235 mg (60%), mp 73°-78°.

Workup

  1. extractionextracted with 50 ml of benzene
  2. extractionextracted 10 times with 50 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e18b820e641540cabc94c5b7b2487909
Source dataset
uspto-grants-1978_05
Patent number
US04089956

Reaction notes

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