Water → Ertapenem

HRID 2067708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2067708
[SH:1][C@@H:2]1[CH2:6][N:5](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:4]([C:20]([NH:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([OH:28])=[O:27])=[O:21])[CH2:3]1.[OH:32][C@@H:33]([C@H:35]1[C:72](=[O:73])[N:37]2[C:38]([C:59]([O:61]CC3C=CC([N+]([O-])=O)=CC=3)=[O:60])=[C:39](OP(OC3C=CC=CC=3)(OC3C=CC=CC=3)=O)[C@H:40]([CH3:41])[C@H:36]12)[CH3:34].C(N(CC)C(C)C)(C)C.O>CN(C=O)C.C(OCC)(=O)C>[CH3:41][C@H:40]1[C:39]([S:1][C@@H:2]2[CH2:6][NH:5][C@H:4]([C:20]([NH:22][C:23]3[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([OH:28])=[O:27])[CH:24]=3)=[O:21])[CH2:3]2)=[C:38]([C:59]([OH:61])=[O:60])[N:37]2[C@H:36]1[C@@H:35]([C@H:33]([OH:32])[CH3:34])[C:72]2=[O:73]

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 10304013(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateHCID 154092601-[(4-Nitrophenyl)methyl] (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylate

Produkt 1

HCID 150610Ertapenem

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 3-[[[(2S,4S)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid (7.68 g) in DMF (30 mL), p-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[(diphenylphosphono)oxy]-1-methylcarbapen-2em-3-carboxylate (10 g) was added. To the reaction mixture N,N-diisopropylethylamine (4.78 g) was added at −30° C. and stirred. After completion of reaction, the reaction mass was poured into water and ethyl acetate mixture at 10° C. The layers were separated and organic layer washed with brine solution. The organic layer was subjected to carbon treatment and taken for subsequent step.

Aufarbeitung

  1. customAfter completion of reaction
  2. customThe layers were separated
  3. washorganic layer washed with brine solution

Quellen und Nachweise

ORD-Eintrag
ord-74a0627d0e6644a7bd9fc3bf79cda160
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293894B2

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