Triethylamine → (6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 483040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483040
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])/[C:27]([OH:29])=O)[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:65][C@@H:66]1[C:84](=[O:85])[N:68]2[C:69]([C:81]([OH:83])=[O:82])=[C:70]([CH2:73][S:74][C:75]3[N:79]([NH2:80])[N:78]=[N:77][N:76]=3)[CH2:71][S:72][C@H:67]12.C(N(CC)CC)C.NC1C(CSC2N(NC(C)C)N=NN=2)=C(C(O)=O)N2C(=O)C[C@H]2S1>CC(N(C)C)=O.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])/[C:27]([NH:65][C@@H:66]2[C:84](=[O:85])[N:68]3[C:69]([C:81]([OH:83])=[O:82])=[C:70]([CH2:73][S:74][C:75]4[N:79]([NH2:80])[N:78]=[N:77][N:76]=4)[CH2:71][S:72][C@H:67]23)=[O:29])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13078701(2Z)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acidHCID 133675107beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidHCID 131714570Amino-3-[(1-isopropylamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid

Produkt 1

HCID 141545485(6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tert-butoxycarbonylmethoxyimino)acetic acid (3.80 g, 7 mmol), 1-hydroxybenzotriazole (1.09 g, 8.05 mmol) and N,N'-dicyclohexylcarbodiimide (1.59 g, 7.7 mmol) in dimethylacetamide (40 ml) was stirred at room temperature for 2 hours. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.76 g, 8.4 mmol) and triethylamine (1.70 g, 16.8 mmol) in dimethylacetamide (20 ml) and water (2.8 ml) and the mixture was stirred at room temperature for 17 hours. Then the mixture was treated in a manner similar to that described in Example 6, (c) to give pale brown powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tert-butoxycarbonylmethoxyimino)acetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (4.96 g, 83%).

Aufarbeitung

  1. additionThen the mixture was treated in a manner similar to

Quellen und Nachweise

ORD-Eintrag
ord-b45f2eddde7844199a0384f3f9ed9b3e
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04576938

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