Sodium (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 → HCID 69467710, compound

HRID 1799756Notes

Reaction equation

[CH2:1]([N:5]([CH:11]([CH3:13])[CH3:12])[C:6](=[O:10])[O:7][CH2:8]Cl)[CH:2]([CH3:4])[CH3:3].[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O-:36])=[O:35])=[C:21]([S:24]/[CH:25]=[CH:26]\[C:27]3[S:31][CH:30]=[N:29][C:28]=3[CH2:32][OH:33])[C@H:22]([CH3:23])[C@H:18]12)[CH3:16].[Na+]>>[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O:36][CH2:8][O:7][C:6]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH:11]([CH3:13])[CH3:12])=[O:10])=[O:35])=[C:21]([S:24]/[CH:25]=[CH:26]\[C:27]3[S:31][CH:30]=[N:29][C:28]=3[CH2:32][OH:33])[C@H:22]([CH3:23])[C@H:18]12)[CH3:16]

Participants

Reactant 2

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

HCID 86609819HCID 86609819, compound

Product 1

HCID 69467710HCID 69467710, compoundYield 67.9%

Procedure

In the same manner as in step b) in Example 125, 279 mg of the title compound was prepared from 177 mg of chloromethyl N-isobutyl-N-isopropylcarbamate and 300 mg of sodium (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.

Sources & evidence

ORD record: ord-e24261c3616b4604899abf288f49ccf9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344154B2

Reaction notes

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