Hydrochloric Acid → HCID 131720416, compound

HRID 727593Notes

Reaction equation

HRID 727593 reaction equation
[C:1]([CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]2[CH2:18][C@H:17]([S:19][C:20]3[C@H:21]([CH3:44])[C@@H:22]4[C@@H:39]([C@H:40]([OH:42])[CH3:41])[C:38](=[O:43])[N:23]4[C:24]=3[C:25]([O:27]CC3C=CC([N+]([O-])=O)=CC=3)=[O:26])[CH2:16][N:15]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=[O:13])[CH2:7][CH2:6]1)(=[O:3])[NH2:2].[ClH:58]>O1CCCC1.O>[ClH:58].[C:1]([CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]2[CH2:18][C@H:17]([S:19][C:20]3[C@H:21]([CH3:44])[C@@H:22]4[C@@H:39]([C@H:40]([OH:42])[CH3:41])[C:38](=[O:43])[N:23]4[C:24]=3[C:25]([OH:27])=[O:26])[CH2:16][NH:15]2)=[O:13])[CH2:7][CH2:6]1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10724092HCID 10724092, compound

Product 1

HCID 131720416HCID 131720416, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

200 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-[(2S, 4S)-2-(4-carbamoylmethyl-1-homopiperazinylcarbonyl)-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 20 ml of a 1:1 by volume mixture of tetrahydrofuran and water, after which 0.18 ml of 1N aqueous hydrochloric acid were added to the mixture, which was then hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 0.3 g of 10% w/w palladium-on-charcoal. The catalyst was then filtered off, and the filtrate was extracted with diethyl ether. The aqueous layer was concentrated by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through a Lobar column (a product of Merck, LiChroprep RP-8, size B), using water as the eluent. Those fractions containing the title compound were combined, concentrated by evaporation under reduced pressure and lyophilized, to give 30 mg of the title compound as a colorless powder.

Workup

  1. customby bubbling hydrogen through it at room temperature for 2 hours in the presence of 0.3 g of 10% w/w palladium-on-charcoal
  2. filtrationThe catalyst was then filtered off
  3. extractionthe filtrate was extracted with diethyl ether
  4. concentrationThe aqueous layer was concentrated by evaporation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through a Lobar column (a product of Merck, LiChroprep RP-8, size B),
  6. additionThose fractions containing the title compound
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4070bcb1f7054b0b8ed30f17f46b883a
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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