Lithium Hydroxide → HCID 66777684, compound

HRID 2091206Notes

Reaction equation

HRID 2091206 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]([CH3:34])[CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[O:25])=[CH:20][CH:19]=3)[CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:7]([CH3:35])[C:6]=2[CH:36]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].[Cl-].[NH4+].[OH-].[Li+]>CN(C)C(=O)C.O.C(O)C.O1CCCC1.C(N(CC)CC)C>[CH:11]1([CH:10]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([N:26]([CH3:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:25])=[CH:20][CH:19]=2)[C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:38]([CH3:37])(=[O:40])=[O:39])=[CH:36][C:6]=3[C:7]=2[CH3:35])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

10

Reactant 4

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 66778821HCID 66778821, compound

Product 1

HCID 66777684HCID 66777684, compoundYield 91%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution (10 mL) of ethyl 3-{[(4-{[(5-amino-3-methyl-1-benzofuran-2-yl)(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (412 mg) synthesized in Example A110(5) in N,N-dimethylacetamide were added triethylamine (160 μL) and methanesulfonyl chloride (89.0 μL), and the mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (60% ethyl acetate/hexane) to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (5 mL), ethanol (5 mL) and water (1 mL) was added 4N lithium hydroxide aqueous solution (500 μL), and the mixture was stirred at room temperature for 4 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 (379 mg, 91%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (60% ethyl acetate/hexane)
  8. customto give a yellow oil
  9. stirringthe mixture was stirred at room temperature for 4 hr
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe residue was dissolved in water (10 mL)
  12. addition1N hydrochloric acid (2.00 mL) was added at 0° C
  13. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-fea1f9d24fa448d59486eb9c7f0c7794
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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