Tetrahydrofuran → HCID 21962494, compound

HRID 1821488Notes

Reaction equation

HRID 1821488 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][S:26]([C:29]2C=CC(C3C=C(C=CC=3)C(OC)=O)=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[C:15]1[CH2:45][CH2:46][NH:47][S:48]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[Cl:58])(=[O:50])=[O:49])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:59]1[CH2:63][O:62][CH2:61][CH2:60]1.[OH-:64].[Na+]>CO>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][S:26]([C:29]2[CH:30]=[CH:31][C:60]([C:61]([OH:64])=[O:62])=[CH:59][CH:63]=2)(=[O:28])=[O:27])=[C:15]1[CH2:45][CH2:46][NH:47][S:48]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[Cl:58])(=[O:50])=[O:49])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21962290HCID 21962290, compound

Product 1

HCID 21962494HCID 21962494, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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) (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-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.

Workup

  1. customSolvents were removed
  2. customcollected
  3. customresulting precipitate
  4. filtrationby filtration

Sources & evidence

ORD record
ord-73a3a41475834755bde31b037e83b3a9
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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