Reaktion #691131

ord-7ca4de1988704d5ab9ad1737886edf1f

Reaktionsgleichung

COC(=O)c1cccc(-c2ccc(S(=O)(=O)CCc3c(CCNS(=O)(=O)Cc4ccccc4Cl)n(C(c4ccccc4)c4ccccc4)c4ccc(Cl)cc34)cc2)c1
Methyl 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-{[(2-chlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]benzoate
C1CCOC1
THF
[Na+].[OH-]
NaOH
→
O=C(O)c1ccc(S(=O)(=O)CCc2c(CCNS(=O)(=O)Cc3ccccc3Cl)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1
4-({2-[1-benzhydryl-5-chloro-2-(2-{[(2-chlorobenzyl)-sulfonyl]amino}ethyl)-1H-indol-3-yl]ethyl}sulfonyl)benzoic acid
Ausbeute 80.0%

Edukte

COC(=O)c1cccc(-c2ccc(S(=O)(=O)CCc3c(CCNS(=O)(=O)Cc4ccccc4Cl)n(C(c4ccccc4)c4ccccc4)c4ccc(Cl)cc34)cc2)c1
Methyl 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-{[(2-chlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]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 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-{[(2-chlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]benzoate (1 eq), THF (0.1M), MeOH (1 mL/1 mL THF), and NaOH (1N) (1 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-5-chloro-2-(2-{[(2-chlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethyl}sulfonyl)benzoic acid (red-orange solid) in 80% yield. HRMS calc for [C39H34Cl2N2O6S2+H] 761.13081 found 761.13146.

Quelle

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