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Triethylamine → 3-Azido-4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one

HRID 1856070
Notes
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Reaction equation

HRID 1856070 reaction equation
C(N(CC)CC)C.C(C1C=CC(S([N:20]=[N+:21]=[N-])(=O)=O)=CC=1)(O)=O.[N:23]([CH:26]1[CH:29]([CH2:30][C:31](=[O:43])[CH2:32][C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[NH:28][C:27]1=[O:44])=[N+:24]=[N-:25]>C(#N)C.C(OC(=O)C)C>[N:23]([CH:26]1[CH:29]([CH2:30][C:31](=[O:43])[C:32]([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])=[N+:20]=[N-:21])[NH:28][C:27]1=[O:44])=[N+:24]=[N-:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86999Benzoic acid, 4-(azidosulfonyl)-HCID 205636593-Azido-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Product 1

HCID 545275133-Azido-4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

Triethylamine (15 mmol) is added to an ice-cold stirring suspension of p-carboxybenzene sulfonylazide (5 mmol) and 3-azido-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one (5 mmol) in anhydrous acetonitrile (30 ml). The resulting mixture is stirred at room temperature for 90 mins, then diluted with ethylacetate and filtered. The filtrate is washed with water, 0.5 N sodium hydroxide, water, and brine, dried over magnesium sulfate, filtered, and evaporated under vacuum to give 3-azido-4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 90 mins
  2. filtrationfiltered
  3. washThe filtrate is washed with water, 0.5 N sodium hydroxide, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-401e51c88d904579b0aa696e1a21b829
Source dataset
uspto-grants-1980_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04217453

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes