Reaktion #2333289

ord-c21d444745df4affbc100cf348adae4d

Reaktionsgleichung

$C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S/C=C\c3nc(CO)cs3)[C@H](C)[C@H]12.[Na+]$

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

1-(cyclohexyloxycarbonyloxy)ethyl iodide

→

$CC(OC(=O)OC1CCCCC1)OC(=O)C1=C(S/C=C\c2nc(CO)cs2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12$

title compound

Ausbeute 89.9%

$CC(OC(=O)OC1CCCCC1)OC(=O)C1=C(S/C=C\c2nc(CO)cs2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12$

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

Ausbeute 89.9%

Edukte

$C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S/C=C\c3nc(CO)cs3)[C@H](C)[C@H]12.[Na+]$

sodium (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-2-yl)ethen-1-yl]thio]-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, 52.7 mg of the title compound was prepared from 42.9 mg of sodium (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-2-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate and 48 mg of 1-(cyclohexyloxycarbonyloxy)ethyl iodide.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07687490B2uspto-grants-2010_03