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Sulfuric Acid → (6R,7R)-3-[[5-amino-4-(aminomethyl)-1-(2-hydroxyethyl)pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrogen sulfate

HRID 349581
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 349581
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:35]/[O:36][C:37]([C:40]([OH:42])=[O:41])([CH3:39])[CH3:38])/[C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([O-:32])=[O:31])=[C:15]([CH2:18][N+:19]4[N:20]([CH2:27][CH2:28][OH:29])[C:21]([NH2:26])=[C:22]([CH2:24][NH2:25])[CH:23]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[S:43](=[O:47])(=[O:46])([OH:45])[OH:44].C(#N)C>O>[S:43]([O-:47])([OH:46])(=[O:45])=[O:44].[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:35]/[O:36][C:37]([C:40]([OH:42])=[O:41])([CH3:39])[CH3:38])/[C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([OH:32])=[O:31])=[C:15]([CH2:18][N+:19]4[N:20]([CH2:27][CH2:28][OH:29])[C:21]([NH2:26])=[C:22]([CH2:24][NH2:25])[CH:23]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 141600997(6R,7R)-3-[[5-amino-4-(aminomethyl)-1-(2-hydroxyethyl)pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Produkt 1

HCID 141601011
(6R,7R)-3-[[5-amino-4-(aminomethyl)-1-(2-hydroxyethyl)pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrogen sulfate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

7β-[(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[3-amino-4-aminomethyl-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (5.0 g) was dissolved in water (100 ml), and 2.0 M sulfuric acid (4.0 ml) was added to the solution. The mixture was freeze-dried to give crude 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[3-amino-4-aminomethyl-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate hydrogensulfate (5.18 g) as an amorphous solid. The amorphous solid (1.0 g) was dissolved in water (1.0 ml). To the solution was added acetonitrile (5.0 ml) dropwise. After stirring at room temperature for 2 hours, white crystals precipitated. The precipitated crystals were collected by filtration on a glass filter, washed with a small amount of water/acetonitrile (1:5) and dried under reduced pressure to give 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[3-amino-4-aminomethyl-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate hydrogensulfate (880 mg) as white crystals. 1H-NMR(D2O) δ1.61(6H, s), 3.20 and 3.53 (2H, ABq, J=18.0 Hz), 3.87 (2H, t, J=4.6 Hz), 4.09 (2H, s), 4.38 (2H, t, J=4.6 Hz), 5.16 (2H, s), 5.28 (1H, d, J=4.8 Hz), 5.88 (1H, d, J=4.8 Hz), 8.10 (1H, s)

Aufarbeitung

  1. customThe mixture was freeze-dried
  2. customto give crude 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[3-amino-4-aminomethyl-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate hydrogensulfate (5.18 g) as an amorphous solid
  3. customwhite crystals precipitated
  4. filtrationThe precipitated crystals were collected by filtration on a glass
  5. filtrationfilter
  6. washwashed with a small amount of water/acetonitrile (1:5)
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbef787820274896a46ba36092d7f8d1
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07179801B2

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