HCID 15200286, compound → HCID 131718816, compound

HRID 1492806Notes

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.Cl.[SH:44][C@@H:45]1[CH2:49][N:48]([C:50]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][CH:55]=2)=[O:51])[C@H:47]([CH:63]2[CH2:66][N:65]([CH3:67])[CH2:64]2)[CH2:46]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:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])=[C:18]([S:44][C@@H:45]3[CH2:49][N:48]([C:50]([O:52][CH2:53][C:54]4[CH:55]=[CH:56][C:57]([N+:60]([O-:62])=[O:61])=[CH:58][CH:59]=4)=[O:51])[C@H:47]([CH:63]4[CH2:64][N:65]([CH3:67])[CH2:66]4)[CH2:46]3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

Reactant 2

HCID 15200286HCID 15200286, compound

HCID 88456925HCID 88456925, compound

Product 1

HCID 131718816HCID 131718816, compoundYield 80.5%

Procedure

The same procedure as in Example 49-1) was carried out by using p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (300 mg, 0.50 mmol) and (2S,4S)-4-mercapto-2-(N-methylazetidin-3-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride (195 mg, 0.50 mmol, compound of Reference Example 42) to obtain p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-(N-methylazetidin-3-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (280 mg, yield: 80% ).

Sources & evidence

ORD record: ord-90a474b06662492792972cbcfc69a2b8
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374720

Reaction notes

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