HCID 15200286, compound → HCID 57218217, compound

HRID 1755723Notes

Reaction equation

O(P(O[C:18]1[C@H:19]([CH3:42])[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.FC(F)(F)S(O)(=O)=O.[SH:51][C@@H:52]1[CH2:56][N:55]([C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][C:64]([N+:67]([O-:69])=[O:68])=[CH:63][CH:62]=2)=[O:58])[C@H:54]([CH:70]2[CH2:74][CH2:73][N:72]([CH3:75])[CH2:71]2)[CH2:53]1>>[OH:40][C@@H:38]([C@H:37]1[C:36](=[O:41])[N:21]2[C:22]([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])=[C:18]([S:51][C@@H:52]3[CH2:56][N:55]([C:57]([O:59][CH2:60][C:61]4[CH:62]=[CH:63][C:64]([N+:67]([O-:69])=[O:68])=[CH:65][CH:66]=4)=[O:58])[C@H:54]([CH:70]4[CH2:74][CH2:73][N:72]([CH3:75])[CH2:71]4)[CH2:53]3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

Reactant 2

HCID 15200286HCID 15200286, compound

HCID 18657909HCID 18657909, compound

Product 1

HCID 57218217HCID 57218217, compoundYield 74.5%

Procedure

The same procedure as in Example 1-1 was carried out by using p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (680 mg, 1.14 mmol) and (2S,4S)-4-mercapto-2-(N-methylpyrrolidin-3-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethane sulfonate (650 mg, 1.26 mmol, compound of Reference Examples 6-9) to obtain p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-N-(p-nitrobenzyloxycarbonyl)-2-(N-methylpyrrolidin-3-yl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (603 mg, yield: 74.3%).

Sources & evidence

ORD record: ord-ed95b94f0aea4194bff37bbbd476fef7
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438054

Reaction notes

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