4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → 5-Methyl-2-oxo-1,3-dioxolen-4-ylmethyl (1R, 5S, 6S)-2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 5065Notes

Reaction equation

HRID 5065 reaction equation
[O:1]=[C:2]1[CH2:6][CH:5]([S:7][C:8]2[CH:9]([CH3:22])[C@@H:10]3[CH:17]([C@H:18]([OH:20])[CH3:19])[C:16](=[O:21])[N:11]3[C:12]=2[C:13]([O-:15])=[O:14])[CH2:4][NH:3]1.[Na+].[CH3:24][C:25]1[O:29][C:28](=[O:30])[O:27][C:26]=1[CH2:31]Br>>[O:1]=[C:2]1[CH2:6][CH:5]([S:7][C:8]2[C@H:9]([CH3:22])[C@@H:10]3[C@@H:17]([C@H:18]([OH:20])[CH3:19])[C:16](=[O:21])[N:11]3[C:12]=2[C:13]([O:15][CH2:31][C:26]2[O:27][C:28](=[O:30])[O:29][C:25]=2[CH3:24])=[O:14])[CH2:4][NH:3]1

Participants

3

Reactant 2

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 131717290sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 1317181135-Methyl-2-oxo-1,3-dioxolen-4-ylmethyl (1R, 5S, 6S)-2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylateYield 79.5%

Procedure

Following a procedure similar to that described in Example 39, but using 50 mg of sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 55 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide, 50 mg of the title compound were obtained as a colorless powder.

Sources & evidence

ORD record
ord-50ea5bd8d6b3424b8c861a6db968fd72
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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