Lithium Hydroxide → 2-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

HRID 1872102Notes

Reaction equation

HRID 1872102 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:27])[C@@H:6]([NH:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=2)=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[Cl:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([C:15]([NH:14][CH:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:27])=[O:4])=[O:16])=[CH:25]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10546217HCID 10546217, compound

Product 1

HCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 2M LiOH (33.10 ml) was added to a solution of (2S)-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (21.47 g, 60 mmol) in THF (140 ml) at 0-5° C. After 0.5 hour, the mixture was partially concentrated, acidified to pH 1-2 with 6N HCl, concentrated to dryness, and the solids washed with water and then etherto yield a colorless solid (18.78g,91%): mp 248-255° C.; HPLC (60/40) 5.21 minutes (98%); TSPMS 343/345 (MH+, 100%).

Workup

  1. concentrationthe mixture was partially concentrated
  2. concentrationconcentrated to dryness
  3. washthe solids washed with water

Sources & evidence

ORD record
ord-71d49058b44644f49651fd64f1ef8cb0
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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