Hydrochloric Acid → HCID 15670486, compound

HRID 257975Notes

Reaction equation

C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:16][C@H:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:14][C@H:13]2/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:7][CH:6]=1)(=O)C.Cl.[OH-].[Na+]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:16][C@H:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)(=[O:19])=[O:20])[CH2:14][C@H:13]2/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:7][CH:6]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 15670469HCID 15670469, compound

Product 1

HCID 15670486HCID 15670486, compoundYield 51.7%

Procedure

A solution of (2S,4R)-1-[(4-acetylaminophenyl)methyl]-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine (200 mg) in 6N-hydrochloric acid (5 ml) was refluxed for 4 hours. The mixture was cooled in an ice bath and adjusted to pH 7 with 1N-sodium hydroxide. The precipitated solid was collected by filtration to give (2S,4R)-1-[(4-aminophenyl)methyl]-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine (95 mg).

Workup

temperatureThe mixture was cooled in an ice bath
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-bf55124b7dc047eab8c4803ad3807124
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264453

Reaction notes

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