Dimethylformamide → 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-ethoxycarbonyl-N-methylaminoethyl ester

HRID 1111755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1111755
[Na].[C:2]([O:5][CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:29])[CH:11]2[NH:15][C:16](=[O:28])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]=[N+:26]=[N-:27])=[CH:20][CH:19]=2)[C:8]=1[C:30]([OH:32])=[O:31])(=[O:4])[CH3:3].Cl[CH2:34][N:35]([CH3:41])[C:36]([O:38][CH2:39][CH3:40])=[O:37].[CH3:42]N(C)C=O>>[CH2:39]([O:38][C:36]([N:35]([CH2:34][CH2:42][O:31][C:30]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[CH2:6][O:5][C:2](=[O:4])[CH3:3])[CH:11]([NH:15][C:16](=[O:28])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]=[N+:26]=[N-:27])=[CH:22][CH:23]=1)[C:10]2=[O:29])=[O:32])[CH3:41])=[O:37])[CH3:40]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 5360545SodiumHCID 15790124Ethyl N-(chloromethyl)-N-methylcarbamateHCID 227677583-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Produkt 1

HCID 541110573-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-ethoxycarbonyl-N-methylaminoethyl ester

Versuchsvorschrift

A mixture of 1.2 g of the sodium salt of 3-[(acetyloxy)-methyl]-7-[[2-[4-(azidomethyl]phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 0.5 g of N-chloromethyl-N-methylurethane in 40 ml of dimethylformamide is stirred at room temperature for 2 hours. The mixture is poured into ice-water and decanted. The oily residue is taken up in 75 ml of ethyl acetate and washed with 5 ml of dilute aqueous sodium bicarbonate and 15 ml of water then dried over magnesium sulfate, filtered and evaporated to give 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-ethoxycarbonyl-N-methylaminoethyl ester.

Aufarbeitung

  1. customdecanted
  2. washwashed with 5 ml of dilute aqueous sodium bicarbonate and 15 ml of water
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c5a0c82c06f9442092166384c273c10b
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04118562

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