HCID 15200286, compound → HCID 57105860, compound

HRID 1492804Notes

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(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:47]([CH:63]2[CH2:68][CH2:67][N:66]([CH3:69])[CH2:65][CH2:64]2)[CH2:46]1>>[CH:36]([N:21]([CH2:20][CH3:19])[CH:22]([CH3:18])[CH3:23])([CH3:37])[CH3:45].[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])=[CH:18][C@@:19]([CH3:42])([S:44][C@@H:45]3[CH2:49][NH:48][C@H:47]([CH:63]4[CH2:68][CH2:67][N:66]([CH3:69])[CH2:65][CH2:64]4)[CH2:46]3)[C@H:20]12)[CH3:39]

Participants

Reactant 2

HCID 15200286HCID 15200286, compound

HCID 88456960HCID 88456960, compound

Product 2

HCID 81531Diisopropylethylamine

HCID 57105860HCID 57105860, compoundYield 79.5%

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 (3.86 g, 6.5 mmol), (2S,4S)-4-mercapto-2-(N-methylpiperidin-4-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride (2.88 g, 6.9 mmol, the compound of Reference Example 38 and N,N-diisopropylethylamine (2.61 ml, 15 mmol) to obtain p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-1-[(2S,4S)-2-(N-methylpiperidin-4-yl)pyrrolidin-4-yl-thio]-1-carbapen-2-em-3-carboxylate (3.74 g, yield: 79.5%). Various spectra data of this compound agreed to the data of the compound obtained in Example 49-1). ##STR1223##

Sources & evidence

ORD record: ord-8a75a9ebddae48a6918d15be1b051608
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374720

Reaction notes

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