(2S,4S)-N-Allyloxycarbonyl-2-hydroxymethyl-4-mercaptopyrrolidine → Allyl (1R,5S,6S)-2-[(2S,4S)-N-allyloxycarbonyl-2-hydroxymethylpyrrolidin-4-ylthio]-6-[(R)-1-allyloxycarbonyloxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 2371832Notes

Reaction equation

HRID 2371832 reaction equation
[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@H:10]1[C:24](=[O:25])[N:12]2[C@@H:13]([C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[C:14](=O)[C@H:15]([CH3:16])[C@@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3].[CH2:26]([O:29][C:30]([N:32]1[CH2:36][C@@H:35]([SH:37])[CH2:34][C@H:33]1[CH2:38][OH:39])=[O:31])[CH:27]=[CH2:28]>>[CH2:26]([O:29][C:30]([N:32]1[CH2:36][C@@H:35]([S:37][C:14]2[C@H:15]([CH3:16])[C@@H:11]3[C@@H:10]([C@H:8]([O:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH3:9])[C:24](=[O:25])[N:12]3[C:13]=2[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[CH2:34][C@H:33]1[CH2:38][OH:39])=[O:31])[CH:27]=[CH2:28]

Participants

3

Reactant 2

HCID 22842694(2S,4S)-N-Allyloxycarbonyl-2-hydroxymethyl-4-mercaptopyrrolidineHCID 131717190allyl (1R,3R,5S,6S)-6-[(R)-1-allyloxycarbonyloxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate

Product 1

HCID 131717189Allyl (1R,5S,6S)-2-[(2S,4S)-N-allyloxycarbonyl-2-hydroxymethylpyrrolidin-4-ylthio]-6-[(R)-1-allyloxycarbonyloxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylateYield 37%

Procedure

The same operation as in Reference Example 9 was carried out by using allyl (1R,3R,5S,6S)-6-[(R)-1-allyloxycarbonyloxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate (700 mg, 2 mmol) and (2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-mercaptopyrrolidine (the compound obtained in Reference Example 1; 470 mg, 1.8 mmol) to obtain the title compound (410 mg, 37% yield).

Workup

  1. customobtained in Reference Example 1

Sources & evidence

ORD record
ord-4daba02e69b3424db0d032c20ae13437
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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