Hydrochloric Acid → Ethanol ammonium hydroxide water

HRID 618151Notes

Reaction equation

HRID 618151 reaction equation
[N:1]1C=CC(CC[CH2:9][C:10](N(CC(O)=O)C)=[O:11])=CC=1.[CH2:18]([O:20][C:21](=[O:36])[CH2:22][C@@H](CCC1C2C(=CC=CC=2)NC=1)[NH2:24])[CH3:19].[OH-:37].[Na+].Cl>CCO>[CH3:9][CH2:10][OH:11].[OH2:20].[NH4+:1].[OH-:37].[CH3:19][CH2:18][O:20][C:21]([CH3:22])=[O:36].[CH3:9][CH2:10][OH:11].[OH2:11].[NH4+:24].[OH-:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867544774-(Pyridin-4-yl)butanoyl-sarcosine 3(R)-[2-(indol-3-yl)ethyl]-beta-alanine ethyl ester

Product 2

HCID 86596525Ethanol ammonium hydroxide waterHCID 86752451EtOAc EtOH H2O NH4OH

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ester 6-3 (400 mg, 0.84 mmol) was dissolved in 4 mL EtOH, then 1 N NaOH (1.7 mL, 1.7 mmol) was added. After 90 min the reaction was neutralized with 1 N HCl (1.7 mL, 1.7 mmol) and concentrated to an oil. Flash chromatography (silica, 50:1:1 EtOH/H2O/NH4OH, then again with 12:10:1:1 EtOAc/EtOH/H2O/NH4OH) provided 6-4.

Workup

  1. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-d26163a8c4e647079453041d3440bcd0
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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