Reaktion #1886895

ord-36966f34aa9149a28d1a7b335be474c6

Reaktionsgleichung

$C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S/C=C\c3scnc3CO)[C@H](C)[C@H]12.[Na+]$

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

1-(cyclohexyloxycarbonyloxy)-2-methylpropan-1-yl iodide

→

$CC(C)C(OC(=O)OC1CCCCC1)OC(=O)C1=C(S/C=C\c2scnc2CO)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12$

title compound

Ausbeute 15.9%

$CC(C)C(OC(=O)OC1CCCCC1)OC(=O)C1=C(S/C=C\c2scnc2CO)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12$

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

Ausbeute 15.9%

Edukte

$C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(S/C=C\c3scnc3CO)[C@H](C)[C@H]12.[Na+]$

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

1-(cyclohexyloxycarbonyloxy)-2-methylpropan-1-yl iodide

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Vorschrift

In the same manner as in Example 81, 84 mg of the title compound was prepared from 367 mg of sodium (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate and 300 mg of 1-(cyclohexyloxycarbonyloxy)-2-methylpropan-1-yl iodide.

Quelle

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