1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-, (4-nitrophenyl)methyl ester, (4R,5R,6S)- → HCID 131717267, compound

HRID 1029781Notes

Reaction equation

[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[CH:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[C:8](=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[N+:27]([C:30]1[CH:58]=[CH:57][C:33]([CH2:34][O:35][C:36]([NH:38][CH2:39][CH:40]([SH:56])[CH2:41][NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>>[CH3:10][C@@H:9]1[C@H:5]2[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:25](=[O:26])[N:6]2[C:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[O:13])=[C:8]1[S:56][CH:40]([CH2:39][NH:38][C:36]([O:35][CH2:34][C:33]1[CH:57]=[CH:58][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=1)=[O:37])[CH2:41][NH:42][C:43]([O:45][CH2:46][C:47]1[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=1)=[O:44]

Participants

Reactant 2

HCID 98853021-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-

HCID 19900953HCID 19900953, compound

Product 1

HCID 131717267HCID 131717267, compoundYield 76.2%

Procedure

1.0 g of p-nitrobenzyl (1R,5R,6S)-6-[1(R)-hydroxyethyl]-1-methyl-2-oxocarbapenam-3-carboxylate and 2.0 g of 1,3-bis(p-nitrobenzyloxycarbonylamino)-2-mercaptopropane were reacted in the same manner as described in Example 1 to give 1.7 g of p-nitrobenzyl (1R,5R,6S)-1-methyl-2-[1,3-bis-(p-nitrobenzyloxycarbonylamino)propan-2-ylthio]-6-[1(R)-hydroxyethyl]carbapen-2-em-3-carboxylate.

Sources & evidence

ORD record: ord-fdfee5a6da364df1b5e8447ce27a26b6
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102997

Reaction notes

Loading…