Water → HCID 22731797, compound

HRID 2301403Notes

Reaction equation

HRID 2301403 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:48])[NH:18][C:19]2([CH2:37][C:38]([NH:40][C:41]3[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=3)=[O:39])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][CH:29]([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])[C:20]2=[O:36])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.S(=O)(=O)(O)O.O.C(OCC)(=O)C>C(O)C>[CH2:31]([O:30][CH:29]([O:33][CH2:34][CH3:35])[CH2:28][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH:18][C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=2)=[O:48])([CH2:37][C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)=[O:39])[C:20]1=[O:36])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 18345354HCID 18345354, compound

Product 1

HCID 22731797HCID 22731797, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22.5 °C

Procedure

3-(N′-(4-t-butyldimethylsilyloxymethylphenyl)ureido)-1-(2,2-diethoxyethyl)-3-((4-methylphenyl)aminocarbonylmethyl) indolin-2-one (308 mg) was dissolved in ethanol (15 mL), concentrated sulfuric acid (10 mg) was added, and the mixture was stirred at 15-30° C. for one hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was dried with anhydrous sodium hydrogensulfate and the solvent was distilled off. The reaction mixture was purified by silica gel column chromatography to obtain 225 mg of the title compound (yield: 88%).

Workup

  1. dry with materialthe organic layer was dried with anhydrous sodium hydrogensulfate
  2. distillationthe solvent was distilled off
  3. customThe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-69ba97aac53b45dd9458e72094002b23
Source dataset
uspto-grants-2002_12
Patent number
US06500854B1

Reaction notes

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