Hydrochloric Acid → HCID 67617732, compound

HRID 727588Notes

Reaction equation

HRID 727588 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:5][CH2:4][N:3]1[C:21]([C@@H:23]1[CH2:27][C@H:26]([S:28][C:29]2[C@H:30]([CH3:53])[C@@H:31]3[C@@H:48]([C@H:49]([OH:51])[CH3:50])[C:47](=[O:52])[N:32]3[C:33]=2[C:34]([O:36]CC2C=CC([N+]([O-])=O)=CC=2)=[O:35])[CH2:25][N:24]1C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=[O:22].[ClH:67]>O1CCCC1.O>[ClH:67].[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:21]([C@@H:23]1[CH2:27][C@H:26]([S:28][C:29]2[C@H:30]([CH3:53])[C@@H:31]3[C@@H:48]([C@H:49]([OH:51])[CH3:50])[C:47](=[O:52])[N:32]3[C:33]=2[C:34]([OH:36])=[O:35])[CH2:25][NH:24]1)=[O:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131720411HCID 131720411, compound

Product 1

HCID 67617732HCID 67617732, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

205 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[(2S)-2-methyl-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, after which 240 μl of 1N aqueous hydrochloric acid were added, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 250 mg of 10% w/w palladium-on-charcoal. The reaction mixture was then worked up and purified by the same procedure as described in Example 7(b), to give 30 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 250 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-e4e126643a13430db897dc3fbf7955e7
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

Loading…