1-Iodoethyl cyclohexyl carbonate → HCID 131728004, compound

HRID 2246122Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[N:7]=[CH:8][S:9][C:10]=1/[CH:11]=[CH:12]\[S:13][C:14]1[C@H:15]([CH3:28])[C@@H:16]2[C@@H:23]([C@H:24]([OH:26])[CH3:25])[C:22](=[O:27])[N:17]2[C:18]=1[C:19]([O-:21])=[O:20])(=[O:3])[CH3:2].[Na+].[CH:30]1([O:36][C:37]([O:39][CH:40](I)[CH3:41])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>>[C:1]([O:4][CH2:5][C:6]1[N:7]=[CH:8][S:9][C:10]=1/[CH:11]=[CH:12]\[S:13][C:14]1[C@H:15]([CH3:28])[C@@H:16]2[C@@H:23]([C@H:24]([OH:26])[CH3:25])[C:22](=[O:27])[N:17]2[C:18]=1[C:19]([O:21][CH:40]([O:39][C:37]([O:36][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:38])[CH3:41])=[O:20])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 111092781-Iodoethyl cyclohexyl carbonate

HCID 69469777HCID 69469777, compound

Product 1

HCID 131728004HCID 131728004, compoundYield 91.8%

Procedure

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.

Sources & evidence

ORD record: ord-6d5d46281fc64e40b9507ef957ce415d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687490B2

Reaction notes

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