HCID 15200286, compound → HCID 57211577, compound

HRID 1492803Notes

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)C(O)=O.[SH:50][C@@H:51]1[CH2:55][N:54](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:53]([CH:69]2[CH2:74][CH2:73][N:72]([CH3:75])[CH2:71][CH2:70]2)[CH2:52]1>C(#N)C.C(N(CC)C(C)C)(C)C>[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:50][C@@H:51]3[CH2:55][NH:54][C@H:53]([CH:69]4[CH2:74][CH2:73][N:72]([CH3:75])[CH2:71][CH2:70]4)[CH2:52]3)[C@H:19]([CH3:42])[C@H:20]12)[CH3:39]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (2.50 g, 4.2 mmol) in acetonitrile (60ml), N,N-diisopropylethylamine was dropwise added in a nitrogen stream under cooling with ice, followed by dropwise adding a solution of (2S,4S)-4-mercapto-2-(N-methylpiperidin-4-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidine trifluoroacetic acid salt (2.30 g, 4.6 mmol, compound of Reference Example 37 in acetonitrile (60 ml). After the mixture was stirred at 0° C. for 15 hours, the precipitate was collected by filtration, washed with acetonitrile and dried to obtain p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2 -[(2S,4S)-2-(N-methylpiperidin-4-yl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (2.12 g, yield: 69.7%).

Workup

temperatureunder cooling with ice
filtrationthe precipitate was collected by filtration
washwashed with acetonitrile
customdried

Sources & evidence

ORD record: ord-23870bb9f9f046d8af2e51aeaf4420f8
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374720

Reaction notes

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