Tetrahydrofuran → HCID 66777477, compound

HRID 2091198Notes

Reaction equation

HRID 2091198 reaction equation
[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:14]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[O:29])=[CH:24][CH:23]=1)[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)#[N:2].O1CCCC1.[OH-].[Na+]>C(O)C>[C:1]([C:3]1[C:7]2[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:14]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:29])=[CH:26][CH:27]=1)[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66777795HCID 66777795, compound

Product 1

HCID 66777477HCID 66777477, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-{[(4-{[(3-cyano-5-methoxy-1-benzofuran-2-yl)(cyclohexyl)methyl]amino}phenyl)carbonyl]amino}propanoate (285 mg) synthesized above, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (1.00 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 (1.00 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (246 mg, 92%) as a pale-yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. addition1N hydrochloric acid (1.00 mL) was added at 0° C
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-2a0832a92d27467b8aa3ac8f6f548ed8
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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