Citric Acid → HCID 54099483, compound

HRID 1532342Notes

Reaction equation

HRID 1532342 reaction equation
[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[C:16]([C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[C:24]([CH2:30][CH2:31][C@@H:32]3[CH2:36][CH2:35][CH2:34][N:33]3[C:37](=[O:49])[CH:38]([CH:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[C:39]([O:41]CC)=[O:40])[N:25]2[CH2:28][CH3:29])=[CH:21][CH:20]=1)(=[NH:18])[NH2:17]>C(O)C>[C:16]([C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[C:24]([CH2:30][CH2:31][C@@H:32]3[CH2:36][CH2:35][CH2:34][N:33]3[C:37](=[O:49])[CH:38]([CH:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[C:39]([OH:41])=[O:40])[N:25]2[CH2:28][CH3:29])=[CH:21][CH:20]=1)(=[NH:17])[NH2:18]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 54330178HCID 54330178, compound

Product 1

HCID 54099483HCID 54099483, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 ml flask, 80 mg of ethyl 3-[(S)-2-[2-(6-amidino-1-ethylindol-2 -yl)ethyl]pyrrolidinyl]-2-cyclopentyl-3-oxopropanoate obtained in Example 33 was dissolved in 20 ml of ethanol, and 10 ml of 2N NaOH was added thereto. The reaction mixture was stirred for 10 hours at room temperature, neutralized with 10% aqueous citric acid solution, and then distilled under reduced pressure to remove the solvent. The residue was then purified with column chromatography [eluent: ethyl acetate/methanol (5:1)] on NH-DM1020 silica to obtain 51 mg of the title compound as a yellowish white solid.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue was then purified with column chromatography [eluent: ethyl acetate/methanol (5:1)] on NH-DM1020 silica

Sources & evidence

ORD record
ord-3ba08a31f78e41abb03d5df25a4be6c5
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

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