Methanol → HCID 18373312, compound

HRID 2301674Notes

Reaction equation

HRID 2301674 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:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[C:15]1[CH2:39][OH:40])([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.CO.[OH-].[Na+]>C1COCC1>[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:32]([C:33]([OH:35])=[O:34])=[CH:37][CH:38]=2)(=[O:28])=[O:27])=[C:15]1[CH2:39][OH:40])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18373336HCID 18373336, compound

Product 1

HCID 18373312HCID 18373312, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 4-({2-[1-benzhydryl-5-chloro-2-(hydroxymethyl)-1H-indol-3-yl]ethyl}sulfonyl)benzoate (1 eq) was dissolved in THF (0.07M). Then MeOH (2.5× the volume of THF) was added, followed by a 1N NaOH solution (2 eq). The reaction was stirred overnight and the solvent was then removed. The resulting residue was dissolved in water and 1N HCl was added until solution was acidic. The resulting white precipitate was collected by filtration and it was the title compound in 76% yield. m/z (M−1) 557.6

Workup

  1. customthe solvent was then removed
  2. dissolutionThe resulting residue was dissolved in water
  3. addition1N HCl was added until solution
  4. filtrationThe resulting white precipitate was collected by filtration and it

Sources & evidence

ORD record
ord-b3186900df764047a77af05a38fa053b
Source dataset
uspto-grants-2002_12
Patent number
US06500853B1

Reaction notes

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