1-Iodoethyl cyclohexyl carbonate → HCID 131728000, compound

HRID 1799706Notes

Reaction equation

[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O-:23])=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].[CH:27]1([O:33][C:34]([O:36][CH:37](I)[CH3:38])=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O:23][CH:37]([O:36][C:34]([O:33][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:35])[CH3:38])=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[S:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

Reactant 2

HCID 111092781-Iodoethyl cyclohexyl carbonate

HCID 69468893HCID 69468893, compound

Product 1

HCID 131728000HCID 131728000, compoundYield 89.9%

Procedure

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.

Sources & evidence

ORD record: ord-c216f9768a904b2c9a0c76b5e0462c3a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344154B2

Reaction notes

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