Tetrahydrofuran → HCID 66777357, compound

HRID 2091268Notes

Reaction equation

HRID 2091268 reaction equation
[CH:1]1([CH:7]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([N:37]([CH3:45])[CH2:38][CH2:39][C:40]([O:42]CC)=[O:41])=[O:36])=[CH:31][CH:30]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([NH:18][S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH:1]1([CH:7]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]([N:37]([CH3:45])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[O:36])=[CH:33][CH:34]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([NH:18][S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66778378HCID 66778378, compound

Product 1

HCID 66777357HCID 66777357, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-[({4-[(cyclohexyl{3-methyl-5-[(phenylsulfonyl)amino]-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)(methyl)amino]propanoate (312 mg) synthesized above, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (2.00 mL), and the mixture was stirred at room temperature for 5 hr, and concentrated under reduced pressure. The residue was dissolved in water (10 mL), and 1N hydrochloric acid (2.00 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (240 mg, 80%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. addition1N hydrochloric acid (2.00 mL) was added at 0° C
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-225af0fae6914d6f82b6d04e3cd10c9f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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