Hydrochloric Acid → HCID 86666297, compound

HRID 1026291Notes

Reaction equation

HRID 1026291 reaction equation
[C:1]([O:4][C:5]1[C:10]([O:11][CH2:12][C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])=[CH:9][CH:8]=[C:7]([C:23]2[O:24][C:25]3[CH:31]=[C:30]([O:32][CH2:33][CH:34]4[CH2:36][CH2:35]4)[CH:29]=[CH:28][C:26]=3[N:27]=2)[N:6]=1)(=O)C.C1COCC1.[OH-].[Li+].Cl>CO>[CH:34]1([CH2:33][O:32][C:30]2[CH:29]=[CH:28][C:26]3[N:27]=[C:23]([C:7]4[N:6]=[C:5]([O:4][CH3:1])[C:10]([O:11][CH2:12][C@@H:13]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH3:14])=[CH:9][CH:8]=4)[O:24][C:25]=3[CH:31]=2)[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67777054HCID 67777054, compound

Product 1

HCID 86666297HCID 86666297, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-2-yl acetate (111 mg), THF (1 mL), methanol (1 mL) and 1M lithium hydroxide aqueous solution (1 mL) was stirred at 0° C. for 2 hr. The reaction mixture was neutralized with 1M hydrochloric acid at 0° C., and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was mixed with toluene (2 mL), methyl iodide (0.021 mL) and silver(I) carbonate (92 mg), and the obtained mixture was stirred at 85° C. for 3 days. To the reaction mixture were further added methyl iodide (0.021 mL) and silver(I) carbonate (92 mg), and the mixture was stirred at 85° C. for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white powder (70.0 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was mixed with toluene (2 mL), methyl iodide (0.021 mL) and silver(I) carbonate (92 mg)
  6. stirringthe obtained mixture was stirred at 85° C. for 3 days
  7. stirringthe mixture was stirred at 85° C. for 4 hr
  8. additionWater was added to the reaction mixture
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe obtained organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dc45acf57bb24948be9d406bdf26fee6
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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