Sodium Hydroxide → HCID 54574145, compound

HRID 1532346Notes

Reaction equation

HRID 1532346 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH2:15][CH2:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][N:18]3[C:23]([C@H:25]3[CH2:29][CH2:28][CH2:27][N:26]3[CH2:30][C:31]([O:33]CC)=[O:32])=[O:24])[N:10]2[CH2:13][CH3:14])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH2:15][CH2:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][N:18]3[C:23]([C@H:25]3[CH2:29][CH2:28][CH2:27][N:26]3[CH2:30][C:31]([OH:33])=[O:32])=[O:24])[N:10]2[CH2:13][CH3:14])=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54386567HCID 54386567, compound

Product 1

HCID 54574145HCID 54574145, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 ml flask; 140 mg of ethyl 2-[(R)-2-[[(S)-2-[2-(6-amidino-1-ethylindol-2-yl)ethyl]piperidyl]carbonyl]pyrrolidinyl]acetate was dissolved in 10 ml of ethanol, and 0.5 ml of 2N NaOH was added thereto. The reaction solution was stirred for 3 hours at room temperature and evaporated under reduced pressure to remove the solvent. The residue was purified with column choromatography [eluent: ethyl acetate/methanol (1:1)] on NH-DM1020 silica to obtain 60 mg of the title compound as a yellowish white solid.

Workup

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

Sources & evidence

ORD record
ord-4b07b08296ee41cb8de56c82f923c783
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

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