Water → HCID 22380703, compound

HRID 895628Notes

Reaction equation

HRID 895628 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:15][CH2:16][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][C:18]1=[O:26])[CH2:12][CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>ClCCl>[CH2:1]([O:8][C:9]([N:11]([CH2:15][CH2:16][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][C:18]1=[O:26])[CH2:12][CH2:13][O:14][S:35]([CH3:34])(=[O:37])=[O:36])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22380620HCID 22380620, compound

Product 1

HCID 22380703HCID 22380703, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[2-[N-(Benzyloxycarbonyl)-N-(2-hydroxyethyl)amino]ethyl]-2,3-dihydro-1H-indol-2-one (256 mg) was dissolved in dichloromethane (5 ml), added with triethylamine (0.20 ml) and methanesulfonyl chloride (0.11 ml) with ice cooling and stirred at room temperature for 1.5 hours. The reaction mixture was added with water (5 ml) and extracted twice with dichloromethane (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:2) to obtain 158 mg of the title compound. Yield: 51%.

Workup

  1. extractionextracted twice with dichloromethane (5 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-e99e7f1bef0a4e4ca7cce2fd11961e1d
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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