Hydrochloric Acid → (1R, 5S, 6S)-2-[(2S, 4S)-2-(4-Acetimidoylpiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid hydrochloride

HRID 361997Notes

Reaction equation

HRID 361997 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@@H:12]2[CH2:16][C@H:15]([S:17][C:18]3[C@H:19]([CH3:32])[C@@H:20]4[C@@H:27]([C@H:28]([OH:30])[CH3:29])[C:26](=[O:31])[N:21]4[C:22]=3[C:23]([OH:25])=[O:24])[CH2:14][NH:13]2)=[O:11])[CH2:6][CH2:5]1)(=[NH:3])[CH3:2].[ClH:33]>O>[ClH:33].[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]([C@@H:12]2[CH2:16][C@H:15]([S:17][C:18]3[C@H:19]([CH3:32])[C@@H:20]4[C@@H:27]([C@H:28]([OH:30])[CH3:29])[C:26](=[O:31])[N:21]4[C:22]=3[C:23]([OH:25])=[O:24])[CH2:14][NH:13]2)=[O:11])[CH2:8][CH2:9]1)(=[NH:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9956142(1R, 5S, 6S)-2-[(2S, 4S)-2-(4-Acetimidoylpiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

Product 1

HCID 67617322(1R, 5S, 6S)-2-[(2S, 4S)-2-(4-Acetimidoylpiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 mg of (1R, 5S, 6S)-2-[(2S, 4S)-2-(4-acetimidoylpiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid [prepared as described in step (b) above] were dissolved in 5 ml of water, after which 0.43 ml of 1N aqueous hydrochloric acid was added. The resulting mixture was worked up and purified by reverse phase column chromatography through 30 ml of Cosmo Sil 75C18 -PREP (a trade mark for a product of Nacalai Tesque), using water as the eluent. Those fractions containing the title compound were combined and lyophilized to give 149 mg of the title compound as a powder.

Workup

  1. custompurified by reverse phase column chromatography through 30 ml of Cosmo Sil 75C18 -PREP (a trade mark for a product of Nacalai Tesque),
  2. additionThose fractions containing the title compound

Sources & evidence

ORD record
ord-96c7b297465341e885620edf08304a28
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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