Lithium Hydroxide → HCID 66777340, compound

HRID 2091205Notes

Reaction equation

HRID 2091205 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH:13]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]([CH3:37])[CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:28])=[CH:23][CH:22]=3)[CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[C:10]([CH3:38])[C:9]=2[CH:39]=1)(=[O:3])[CH3:2].O1CCCC1.[OH-].[Li+]>C(O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH:13]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([N:29]([CH3:37])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:25][CH:26]=3)[CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[C:10]([CH3:38])[C:9]=2[CH:39]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 8028TetrahydrofuranHCID 66778230HCID 66778230, compound

Product 1

HCID 66777340HCID 66777340, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-[{[4-({[5-(acetylamino)-3-methyl-1-benzofuran-2-yl](cyclohexyl)methyl}amino)phenyl]carbonyl}(methyl)amino]-propanoate (366 mg) synthesized above, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N lithium hydroxide aqueous solution (1.00 mL), and the mixture was stirred at room temperature for 1 hr. 1N Lithium hydroxide aqueous solution (1.00 mL) was additionally added, and the mixture was stirred at room temperature for 1 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 (292 mg, 84%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-f811751dfc004334a15cf1dcebdad1ed
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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