Reaktion #691130

ord-f4ab1e67e71748b7bdac43b0129ba4cb

Reaktionsgleichung

COC(=O)c1ccc(S(=O)(=O)CCc2c(CCNS(=O)(=O)Cc3ccccc3)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1
Methyl 4-{[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethyl]sulfonyl}benzoate
C1CCOC1
THF
[Na+].[OH-]
NaOH
→
O=C(O)c1ccc(S(=O)(=O)CCc2c(CCNS(=O)(=O)Cc3ccccc3)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1
4-([2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]-ethyl)-5-chloro-1H-indol-3-yl)ethyl]sulfonyl}benzoic acid
Ausbeute 92.0%

Edukte

COC(=O)c1ccc(S(=O)(=O)CCc2c(CCNS(=O)(=O)Cc3ccccc3)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1
Methyl 4-{[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethyl]sulfonyl}benzoate
C1CCOC1
THF
[Na+].[OH-]
NaOH

Reagenzien

Keine

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeSolvents were removed
  2. 2
    Sonstigecollected
  3. 3
    Sonstigeresulting precipitate
  4. 4
    Filtrationby filtration

Vorschrift

Methyl 4-{[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethyl]sulfonyl}benzoate (1 eq), THF (0.1M), MeOH (1 mL/1 mL THF), and NaOH (1N) (11 eq) were stirred together overnight. Solvents were removed and the resulting residue was taken up in water. The solution was acidified with 1N HCl and collected resulting precipitate by filtration. Obtained 4-{[2-(1-benzhydryl-2-{2-[(benzylsulfonyl)amino]ethyl}-5-chloro-1H-indol-3-yl)ethyl]sulfonyl}benzoic acid (off-white solid) in 92% yield. HRMS calc for [C39H35ClN2O6S2—H] 725.15523 found 725.15437.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07906548B2uspto-grants-2011_03