Hydrochloric Acid → HCID 50919235, compound

HRID 1851894Notes

Reaction equation

HRID 1851894 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([O:39]CC)=[O:38])=[CH:33][CH:32]=4)=[CH:27][CH:26]=2)[CH:19]=[CH:18]3)=[O:14])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]4[CH:32]=[CH:33][C:34]([C:37]([OH:39])=[O:38])=[CH:35][CH:36]=4)=[CH:27][CH:26]=2)[CH:19]=[CH:18]3)=[O:14])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 50919239HCID 50919239, compound

Product 1

HCID 50919235HCID 50919235, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-ethyl 4′-((5-((1-(4-nitrophenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)-[1,1′-biphenyl]-4-carboxylate (23 mg, 0.04 mmol, 1 equiv) in MeOH (1 mL) was added 100 L of a 5 N NaOH solution. The mixture is stirred at room temperature overnight and then hydrolyzed by addition of a 1 N HCl solution. After concentration, the crude is purified by preparative HPLC to afford a beige powder (9 mg, 0.02 mmol, 43%). ESI-MS (m/z): 520 [M+H]+.

Workup

  1. concentrationAfter concentration
  2. customthe crude is purified by preparative HPLC

Sources & evidence

ORD record
ord-403a198e7b33483c9fa94bcfb12a3a59
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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