Sodium Hydroxide → HCID 54008685, compound

HRID 1252208Notes

Reaction equation

HRID 1252208 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[Na+].C(O)(=S)C.[OH-].[Na+].[N+:12]([C:15]1[CH:36]=[CH:35][C:18]([CH2:19][O:20][C:21]([O:23][CH:24]([CH:26]2[CH:29](OC(=O)C)[NH:28][C:27]2=[O:34])[CH3:25])=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13]>O1CCOCC1.O.ClCCl>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][C:21]([O:23][CH:24]([CH:26]2[CH:29]([S:3][C:1](=[O:4])[CH3:2])[NH:28][C:27]2=[O:34])[CH3:25])=[O:22])=[CH:35][CH:36]=1)([O-:14])=[O:13]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 15573252HCID 15573252, compoundHCID 23700354HCID 23700354, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 54008685HCID 54008685, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium thioacetate, prepared by treating a solution of thioacetic acid (3.24 g) in dioxane (8 ml) and water (21.5 ml) with 1N aqueous sodium hydroxide, was added to a solution of 3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-acetoxy-2-azetidinone (15.0 g) in dioxane (56 ml) at 0° to 10° C. under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 15 minutes, diluted with ice-cooled dichloromethane, washed with water, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-acetylthio-2-azetidinone.

Workup

  1. additiondiluted with ice-
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give an oily residue which
  6. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-b75e162249c44f17b66f5c437274f4f9
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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