Trifluoroacetic acid → TFA acetonitrile

HRID 582694

Reaktionsgleichung

Reaktionsgleichung von HRID 582694
C([O:5][C:6](=[O:41])[C@@H:7]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:8][NH:9][C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH2:17][N:16]([C@H:21]([CH3:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:15]2=[O:30])=[O:11])(C)(C)C.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>C(Cl)Cl>[OH2:5].[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].[CH3:7][C:8]#[N:9].[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].[O:30]=[C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([C:10]([NH:9][CH2:8][C@H:7]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:6]([OH:41])=[O:5])=[O:11])[CH:13]=2)[CH2:17][N:16]1[C@H:21]([CH3:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1

Komponenten

6

Edukt 2

HCID 6422Trifluoroacetic acidHCID 867542673-Oxo-2-[1(R)-methyl-2(pyridin-2-yl)ethyl]-2,3-dihydro-1-H-isoindole-5-carbonyl-2(S)phenylsulfonylamino-beta-alanine t-butyl ester

Produkt 3

HCID 21924481TFA acetonitrileHCID 22392675Trifluoroacetic acid waterHCID 867542663-Oxo-2-[1(R)-methyl-2(pyridin-2-yl)ethyl]-2,3-dihydro-1-H-isoindole-5-carbonyl-2(S)phenylsulfonylamino-beta-alanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A CH2Cl2 solution (20 mL) of 7-7 (44 mg, 0.074 mmol) and TFA (4 mL) was stirred under ambient conditions for 5 h and then concentrated. The residue was azeotroped with toluene (3×25 mL) to give a solid which was purified by HPLC using a VYDAC C18 semiprep column with gradient elution [95:5 (99.9:0.1 H2O/TFA)/(99.9:0.1 CH3CN/TFA)→50:50 (99.9:1 H2O/TFA) (99.9:1 CH3CN/TFA) 60 min] to provide 7-8 as a colorless solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was azeotroped with toluene (3×25 mL)
  3. customto give a solid which
  4. customwas purified by HPLC
  5. washwith gradient elution [95:5 (99.9:0.1 H2O/TFA)/(99.9:0.1 CH3CN/TFA)→50

Quellen und Nachweise

ORD-Eintrag
ord-c25231d2a5f7441f9d9c6ef2c5c1ddf6
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925655

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