Reaktion #1886903

ord-26754ef6861543378b8583a2feff179d

Reaktionsgleichung

$CC(=O)OCc1ncsc1/C=C\SC1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](C)O)[C@H]2[C@H]1C.[Na+]$

sodium (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

$CC(=O)OCc1ncsc1/C=C\SC1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](C)O)[C@H]2[C@H]1C.[Na+]$

Sodium (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

1-(cyclohexyloxycarbonyloxy)ethyl iodide

→

$CC(=O)OCc1ncsc1/C=C\SC1=C(C(=O)OC(C)OC(=O)OC2CCCCC2)N2C(=O)[C@H]([C@@H](C)O)[C@H]2[C@H]1C$

title compound

Ausbeute 91.8%

$CC(=O)OCc1ncsc1/C=C\SC1=C(C(=O)OC(C)OC(=O)OC2CCCCC2)N2C(=O)[C@H]([C@@H](C)O)[C@H]2[C@H]1C$

1-(Cyclohexyloxycarbonyloxy)ethyl (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Ausbeute 91.8%

Edukte

$CC(=O)OCc1ncsc1/C=C\SC1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](C)O)[C@H]2[C@H]1C.[Na+]$

sodium (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

$CC(=O)OCc1ncsc1/C=C\SC1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](C)O)[C@H]2[C@H]1C.[Na+]$

Sodium (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

1-(cyclohexyloxycarbonyloxy)ethyl iodide

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Vorschrift

In the same manner as in Example 81, 159 mg of the title compound was prepared from 130 mg of sodium (1R,5S,6S)-2-[[(Z)-2-(4-acetoxymethylthiazol-5-yl)ethen-1-yl]thio]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate prepared in Example 79 and 104 mg of 1-(cyclohexyloxycarbonyloxy)ethyl iodide.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08344154B2uspto-grants-2013_01