Trifluoroacetic acid → Water TFA acetonitrile

HRID 583689Notes

Reaction equation

HRID 583689 reaction equation
[C:1](O)(=[O:3])[CH3:2].C([O:9]C(=O)[C@@H:11](NS(C1C=CC=CC=1)(=O)=O)[CH2:12][NH:13]C(=O)C1C=CC(CCC2NC=CN=2)=CC=1)(C)(C)C.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>C(Cl)Cl>[CH3:2][CH2:1][OH:3].[NH4+:13].[OH-:9].[OH2:41].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41].[OH2:3].[CH3:11][C:12]#[N:13]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867543374-[2-(Imidazol-2-yl)ethyl]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester acetate

Product 2

HCID 22145617Water TFA acetonitrileYield 0.1%HCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 23-6 (100 mg, 0.2 mmol) was dissolved in 5 mL CH2Cl2, and 5 mL TFA was added. After 1 h the reaction was concentrated and azeotroped with toluene. Flash chromatography (silica, 50:1:1 EtOH/NH4OH/H2O) and preparative HPLC (C18, 0.1 % TFA H2O/CH3CN) provided 23-7.

Workup

  1. concentrationAfter 1 h the reaction was concentrated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-127f41cd1a5d4e7faa752a421fbedc4b
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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