Hydrochloric Acid → trans-4-[(3-Indolylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylic acid

HRID 1034246Notes

Reaction equation

HRID 1034246 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH:13][C@H:14]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C@H:15]2[C:26]([O:28]CC)=[O:27])=[O:12])=[CH:2]1.C1COCC1.CCO.[OH-].[Li+].Cl>O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH:13][C@@H:14]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C@H:15]2[C:26]([OH:28])=[O:27])=[O:12])=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 67794878Ethyl cis-4-[(1H-indol-3-ylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Product 1

HCID 67794351trans-4-[(3-Indolylacetyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylic acidYield 25.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the title compound of example 8 (520 mg, 1.28 mmol) in 1:4 THF/EtOH (20 ml) was added lithium hydroxide (46 mg (1.92 mmol) in H2O (10 ml) and stirred for 2.5 h. The reaction mixture was acidified with 1N HCl to pH 3 and concentrated in vacuo. The mixture was purified by chromatography on silica gel (CH3OH/HOAc/CH2Cl2 gradient 10/1/89 to 20/1/79) to give 124 mg (18%) of the title compound. MS calcd for C21H19N3O4 : 377, found 377.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe mixture was purified by chromatography on silica gel (CH3OH/HOAc/CH2Cl2 gradient 10/1/89 to 20/1/79)

Sources & evidence

ORD record
ord-a6f38ce5cd6f4a96aecc0ccb8e43b71b
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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