4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 69469394, compound

HRID 1799739Notes

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

Participants

Reactant 2

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

HCID 23676797Sodium (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

Product 1

HCID 69469394HCID 69469394, compoundYield 79.7%

Procedure

In the same manner as in Example 81, 156 mg of the title compound was prepared from 160 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 122 mg of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl bromide.

Sources & evidence

ORD record: ord-7559608c6c0a4ac482c2356f4539e451
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344154B2

Reaction notes

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