Triethylamine → HCID 57278972, compound

HRID 893178Notes

Reaction equation

HRID 893178 reaction equation
[CH2:1]([CH:10]([CH2:49][C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)[N:11]1[CH:14]([CH2:15][C:16](=[O:31])[CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[CH:13]([CH:32]([O:34][C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[O:36])[CH3:33])[C:12]1=[O:48])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(C1C=CC(S([N:70]=[N+:71]=[N-])(=O)=O)=CC=1)(O)=O.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH2:49]([CH:10]([CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[N:11]1[CH:14]([CH2:15][C:16](=[O:31])[C:17]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[O:19])=[N+:70]=[N-:71])[CH:13]([CH:32]([O:34][C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)=[O:36])[CH3:33])[C:12]1=[O:48])[C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86999Benzoic acid, 4-(azidosulfonyl)-HCID 57077533HCID 57077533, compound

Product 1

HCID 57278972HCID 57278972, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.9 g of 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]-2-azetidinone and 660 mg of p-carboxybenzenesulfonyl azide were dissolved in 50 ml of dried acetonitrile, and 1.4 ml of triethylamine was added thereto dropwise in a nitrogen stream under ice-cooling. After stirring at that temperature for 15 minutes, the reaction mixture was diluted with ethyl acetate, and the thus formed precipitate was filtered. The filtrate was concentrated under reduced pressure, and the resulting oily residue was subjected to silica gel chromatography to obtain 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxo-3-diazopropyl]-2-azetidinone.

Workup

  1. temperaturedropwise in a nitrogen stream under ice-cooling
  2. filtrationthe thus formed precipitate was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b49636ef87f45229ef4b2912f0d4350
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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