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Ammonia → 6-(1-Hydroxyethyl)-4-methyl-7-oxo-3-({5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid--water (1/1)

HRID 2094649
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2094649
[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([CH2:16][NH:17][S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12]2)=[C:8]([C:22]([OH:24])=[O:23])[N:7]2[C@H:3]1[C@@H:4]([C@H:25]([OH:27])[CH3:26])[C:5]2=[O:6].N>O>[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([CH2:16][NH:17][S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12]2)=[C:8]([C:22]([OH:24])=[O:23])[N:7]2[C@H:3]1[C@@H:4]([C@H:25]([OH:27])[CH3:26])[C:5]2=[O:6].[OH2:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 73303Doripenem

Produkt 1

HCID 6363776-(1-Hydroxyethyl)-4-methyl-7-oxo-3-({5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid--water (1/1)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Doripenem (50 g) was dissolved in water (300 ml) by adding ammonia drop-wise to attain a pH of 8.5 to 9 at 15° to 20° C. The solution was treated with activated carbon (5 g) followed by micron filtration using a membrane (0.25 microns). The pH of the filtrate was adjusted to 5 to 5.5 with aqueous formic acid at 10° to 20° C. The mixture was stirred at 0° to 5° C. for 4 to 5 hours. Isopropyl alcohol (150 ml) was added slowly to the mixture and stirred for about 12 hours at 0° to 5° C. The mixture was filtered and dried at 40° to 50° C. to obtain the title compound.

Aufarbeitung

  1. customat 15° to 20° C
  2. additionThe solution was treated with activated carbon (5 g)
  3. filtrationfollowed by micron filtration
  4. customwas adjusted to 5 to 5.5 with aqueous formic acid at 10° to 20° C
  5. additionIsopropyl alcohol (150 ml) was added slowly to the mixture
  6. stirringstirred for about 12 hours at 0° to 5° C
  7. filtrationThe mixture was filtered
  8. customdried at 40° to 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-d3bdc0038b2b4ffe8cca1bb7b0b6ab5b
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08445673B2

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