iodoMethyl 2-Methylpropanoate → (1R, 5S, 6S)-2-[(3S)-pyrrolidine-2-thion-3-ylthio]-6-[(1R)-1-hydroxyethy l]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester

HRID 248208Notes

Reaction equation

HRID 248208 reaction equation
[K+].[NH:2]1[CH2:6][CH2:5][C@H:4]([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])=[O:14])[C:3]1=[S:23].[C:24]([O:29][CH2:30]I)(=[O:28])[CH:25]([CH3:27])[CH3:26]>>[C:24]([O:29][CH2:30][O:14][C:13]([C:12]1[N:11]2[C:16](=[O:21])[C@H:17]([C@H:18]([OH:20])[CH3:19])[C@H:10]2[C@@H:9]([CH3:22])[C:8]=1[S:7][C@H:4]1[CH2:5][CH2:6][NH:2][C:3]1=[S:23])=[O:15])(=[O:28])[CH:25]([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 10376456iodoMethyl 2-MethylpropanoateHCID 131717564(1R, 5S, 6S)-2-[(3S)-pyrrolidine-2-thion-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-met hylcarbapen-2em-3-carboxylic acid potassium salt

Product 1

HCID 131717563(1R, 5S, 6S)-2-[(3S)-pyrrolidine-2-thion-3-ylthio]-6-[(1R)-1-hydroxyethy l]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester

Procedure

In the same manner as described in Example 48, (1R, 5S, 6S)-2-[(3S)-pyrrolidine-2-thion-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-met hylcarbapen-2em-3-carboxylic acid potassium salt is treated with isobutyryloxymethyl iodide to give (1R, 5S, 6S)-2-[(3S)-pyrrolidine-2-thion-3-ylthio]-6-[(1R)-1-hydroxyethy l]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester. hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid

Sources & evidence

ORD record
ord-fd9dd8908d944516b4898655f8e0dd35
Source dataset
uspto-grants-1993_05
Patent number
US05208348

Reaction notes

Loading…