Hydrochloric Acid → HCID 24881865, compound

HRID 1821482Notes

Reaction equation

HRID 1821482 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][CH2:36][C:37]([O:39]C)=[O:38])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[C:15]1[CH2:41][CH2:42][NH:43][S:44]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=1)(=[O:46])=[O:45])([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.[OH-].[Na+].Cl>C1COCC1.CO.O>[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][CH2:36][C:37]([OH:39])=[O:38])=[CH:31][CH:30]=2)(=[O:27])=[O:28])=[C:15]1[CH2:41][CH2:42][NH:43][S:44]([CH2:47][C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=1)(=[O:46])=[O:45])([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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21962514HCID 21962514, compound

Product 1

HCID 24881865HCID 24881865, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino} ethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]propanoate (step 13, 1.0 eq) was dissolved in THF:MeOH (1:1) (0.1M), then added 1N NaOH. The mixture was kept stirred overnight at room temperature. The solvent was stripped off and the residue was dissolved in water to form a basic solution, which was neutralized with diluted HCl solution to precipitate the product. The solid was collected by filtration, washed with water, rinsed with hexane, then dried to give the desired product in 86% yield. HRMS calc for [C41H37Cl3N2O6S2+H] 823.12314 found 823.12292.

Workup

  1. customto form a basic solution, which
  2. customto precipitate the product
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. washrinsed with hexane
  6. customdried

Sources & evidence

ORD record
ord-505e8c7bbb7e4f2eb0b525b220143a73
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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