2-(4-Nitrobenzyloxycarbonylaminosulfonyl)aminoethanol → (1s,5r,6s)-6-((1r)-1-Hydroxyethyl)-1-methyl-2-[7-[1-(2-sulfamoylaminoethyl)pyridinium-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate

HRID 1072396Notes

Reaction equation

HRID 1072396 reaction equation
[N+](C1C=CC(COC([NH:12][S:13]([NH:16][CH2:17][CH2:18]O)(=[O:15])=[O:14])=O)=CC=1)([O-])=O.[OH:22][C@@H:23]([C@H:25]1[C:61](=[O:62])[N:27]2[C:28]([C:48]([O:50]CC3C=CC([N+]([O-])=O)=CC=3)=[O:49])=[C:29]([C:32]3[S:36][C:35]4=[C:37]([C:40]([C:42]5[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=5)=[O:41])[N:38]=[CH:39][N:34]4[CH:33]=3)[C@H:30]([CH3:31])[C@H:26]12)[CH3:24]>>[OH:22][C@@H:23]([C@H:25]1[C:61](=[O:62])[N:27]2[C:28]([C:48]([O-:50])=[O:49])=[C:29]([C:32]3[S:36][C:35]4=[C:37]([C:40]([C:42]5[CH:43]=[N+:44]([CH2:18][CH2:17][NH:16][S:13](=[O:15])(=[O:14])[NH2:12])[CH:45]=[CH:46][CH:47]=5)=[O:41])[N:38]=[CH:39][N:34]4[CH:33]=3)[C@H:30]([CH3:31])[C@H:26]12)[CH3:24]

Participants

3

Reactant 2

HCID 223904002-(4-Nitrobenzyloxycarbonylaminosulfonyl)aminoethanolHCID 68934911(4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 10144305(1s,5r,6s)-6-((1r)-1-Hydroxyethyl)-1-methyl-2-[7-[1-(2-sulfamoylaminoethyl)pyridinium-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylateYield 17.7%

Procedure

The title compound (101 mg) was prepared in the same manner as in steps a) and b) of Example 4, except that 572 mg of 2-(4-nitrobenzyloxycarbonylaminosulfonyl)aminoethanol was used instead of 3-azido-1-propanol in step a) of Example 4 and 585 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate was used as the starting compound.

Sources & evidence

ORD record
ord-695c5ddf3fbe443c9a8555c3b035c538
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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