Water → HCID 22731797, compound

HRID 2083882Notes

Reaction equation

HRID 2083882 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-c5162c4ad99a426eb20a5acafc0de362
Source dataset
uspto-grants-2004_04
Patent number
US06716628B2

Reaction notes

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