Tetrahydrofuran → HCID 21962498, compound

HRID 1008646Notes

Reaction equation

HRID 1008646 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]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]([CH3:43])([CH3:42])[C:37]([O:39]CC)=[O:38])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[C:15]1[CH2:44][CH2:45][NH:46][S:47]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=1)(=[O:49])=[O:48])([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.C1COCC1.[OH-].[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:34]=[CH:33][C:32]([CH2:35][C:36]([CH3:43])([CH3:42])[C:37]([OH:39])=[O:38])=[CH:31][CH:30]=2)(=[O:27])=[O:28])=[C:15]1[CH2:44][CH2:45][NH:46][S:47]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([Cl:58])[CH:52]=1)(=[O:49])=[O:48])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21962452HCID 21962452, compound

Product 1

HCID 21962498HCID 21962498, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino)-ethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]-2,2-dimethylpropanoate (0.04 g, 0.05 mmol), THF (0.5 mL), MeOH (0.5 mL), and 1N NaOH (0.5 mL) were stirred together overnight. Solvents were removed and the resulting residue was taken up in water. The solution was acidified with 1N HCl and extracted with ethyl acetate. The extract was dried over sodium sulfate, and evaporated. The resulting residue was triturated with a mixture of ether and hexanes to give 0.04 g of 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)-sulfonyl]amino}ethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]-2,2-dimethylpropanoic acid as a white solid; mp 207-208° C.; MS (ESI) m/z 849.1 (M−H); HRMS: calcd for C43H41Cl3N2O6S2, 850.1472; found (ESI+), 851.1545.

Workup

  1. customSolvents were removed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. customevaporated
  5. customThe resulting residue was triturated with a mixture of ether and hexanes

Sources & evidence

ORD record
ord-8dc1a4163dd94ffa81a59f5cc65e1422
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

Loading…