HCID 131720424, compound → (1R, 5S, 6S)-2-[(2S, 4S)-2-(3-Carboxy-1-piperazinylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

HRID 362007Notes

Reaction equation

HRID 362007 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH:12]2[N:17](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:16][CH2:15][N:14]([C:31]([C@@H:33]3[CH2:37][C@H:36]([S:38][C:39]4[C@H:40]([CH3:63])[C@@H:41]5[C@@H:58]([C@H:59]([OH:61])[CH3:60])[C:57](=[O:62])[N:42]5[C:43]=4[C:44]([O:46]CC4C=CC([N+]([O-])=O)=CC=4)=[O:45])[CH2:35][N:34]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:32])[CH2:13]2)=[O:11])=CC=1)([O-])=O>O1CCCC1.O>[C:10]([CH:12]1[NH:17][CH2:16][CH2:15][N:14]([C:31]([C@@H:33]2[CH2:37][C@H:36]([S:38][C:39]3[C@H:40]([CH3:63])[C@@H:41]4[C@@H:58]([C@H:59]([OH:61])[CH3:60])[C:57](=[O:62])[N:42]4[C:43]=3[C:44]([OH:46])=[O:45])[CH2:35][NH:34]2)=[O:32])[CH2:13]1)([OH:11])=[O:9]

Participants

4

Reactant 1

HCID 131720424HCID 131720424, compound

Product 1

HCID 67618232(1R, 5S, 6S)-2-[(2S, 4S)-2-(3-Carboxy-1-piperazinylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acidYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

160 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[3-(4-nitrobenzyloxycarbonyl)-4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (a) above] were dissolved in 3 ml of a 1:1 by volume mixture of tetrahydrofuran and water, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 160 mg of 10% w/w palladium-on-charcoal. At the end of this time, the reaction mixture was worked up and purified by the same procedure as described in Example 7(b), to give 35 mg of the title compound, as a powder.

Workup

  1. customby bubbling hydrogen through it at room temperature for 2 hours in the presence of 160 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-36899c4c3a654b0892f709343d2befb2
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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