Diisopropylethylamine → HCID 56991637, compound
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.C(N(CC)C(C)C)(C)C.Cl.Cl.[CH2:54]([N:56]1[CH2:60][CH2:59][CH:58]([C@@H:61]2[CH2:65][C@H:64]([SH:66])[CH2:63][NH:62]2)[CH2:57]1)[CH3:55]>C(#N)C.CN(C)C=O>[CH2:54]([N:56]1[CH2:60][CH2:59][CH:58]([C@@H:61]2[CH2:65][C@H:64]([S:66][C:18]3[C@H:19]([CH3:42])[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:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])[CH2:63][NH:62]2)[CH2:57]1)[CH3:55]Participants
Conditions
- Temperature
- -20 °C
Procedure
Under a nitrogen atmosphere at -20 ° C., to a solution of p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (13.76 g, 23.1 mmol) in acetonitrile (150 ml) was added N,N-diisopropylethylamine (13.44 ml, 77.1 mmol), followed by a suspension of (2S,4S)-2-(N-ethylpyrrolidin-3-yl)-4-mercaptopyrrolidine dihydrochloride (7.0 g, 25.7 mmol, compound of Reference Example 40 in N,N-dimethylformamide (40 ml). After stirring overnight at -20° C., the reaction mixture was concentrated in vacuo. The resulting precipitate was collected by filtration, and washed with acetonitrile (30 ml) followed by isopropyl ether (30 ml) to obtain p-nitrobenzyl (1R,5S,6S)-2-[(2S, 4S)-2-(N-ethylpyrrolidin-3-yl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (10.1 g, yield: 72%) as a crude crystal.
Workup
- concentrationthe reaction mixture was concentrated in vacuo
- filtrationThe resulting precipitate was collected by filtration
- washwashed with acetonitrile (30 ml)
Sources & evidence
- ORD record
- ord-6e84ec0438954b118c6d49075c844939
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374720
Reaction notes
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