Tetrahydrofuran → HCID 21962494, compound

HRID 603949Notes

Reaction equation

HRID 603949 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) (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.

Workup

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

Sources & evidence

ORD record
ord-7ca4de1988704d5ab9ad1737886edf1f
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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