p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate → HCID 131718814, compound

HRID 1492797Notes

Reaction equation

HRID 1492797 reaction equation
O(P(O[C:18]1[CH2:19][C@@H:20]2[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]2[C:22]=1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])(OC1C=CC=CC=1)=O)C1C=CC=CC=1.[O:42]=[C:43]1[NH:47][C:46](=[O:48])[CH:45]([C@@H:49]2[CH2:53][C@H:52]([S:54]CC3C=CC(OC)=CC=3)[CH2:51][N:50]2[C:64]([O:66][CH2:67][C:68]2[CH:73]=[CH:72][C:71]([N+:74]([O-:76])=[O:75])=[CH:70][CH:69]=2)=[O:65])[NH:44]1>>[O:42]=[C:43]1[NH:47][C:46](=[O:48])[CH:45]([C@@H:49]2[CH2:53][C@H:52]([S:54][C:18]3[CH2:19][C@@H:20]4[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]4[C:22]=3[C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=3)=[O:24])[CH2:51][N:50]2[C:64]([O:66][CH2:67][C:68]2[CH:73]=[CH:72][C:71]([N+:74]([O-:76])=[O:75])=[CH:70][CH:69]=2)=[O:65])[NH:44]1

Participants

3

Reactant 2

HCID 11319187p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylateHCID 15200304HCID 15200304, compound

Product 1

HCID 131718814HCID 131718814, compoundYield 18%

Procedure

The same procedure as in Example 1-1 was carried out by using p-nitrobenzyl (5R,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (150 mg, 0.258 mmol) and (2S,4S)-2-(2,4-dioxoimidazolidin-5-yl)-4-(p-methoxybenzylthio)-N-(p-nitrobenzyloxycarbonyl)pyrrolidine (120 mg, 0.240 mmol, compound of Reference Example 28) to obtain p-nitrobenzyl (5R,6S)-2-[(2S,4S)-2-(2,4-dioxoimidazolidin-5-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (30 mg, yield: 18%).

Sources & evidence

ORD record
ord-5bf2f24115c5466097df7cc545a1ee43
Source dataset
uspto-grants-1994_12
Patent number
US05374720

Reaction notes

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