HCID 68507742, compound → HCID 59529343, compound

HRID 1877190Notes

Reaction equation

HRID 1877190 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH3:14])=[C:11]([CH:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:28])=[CH:23][CH:22]=3)[CH2:16][CH:17]([CH3:19])[CH3:18])[CH:10]=2)=[CH:5][CH:4]=1>C(O)C.CCCCCC>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH3:14])=[C:11]([CH:15]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:25][CH:26]=3)[CH2:16][CH:17]([CH3:19])[CH3:18])[CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 68507742HCID 68507742, compound

Product 1

HCID 59529343HCID 59529343, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

Ethyl 3-({[4-({1-[5-(6-methoxypyridin-3-yl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}amino)propanoate (1000 mg) which is a synthetic intermediate in Example 148 was dissolved in ethanol-hexane (1:1, volume ratio), and the solution was subjected to HPLC using CHIRALPAK AD (50 mmID×500 mmL, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.) and eluted with ethanol-hexane (1:1, volume ratio) as mobile phase at 30° C., a flow rate 60 mL/min. The fractions showing a peak with retention time 11.5 min were collected, and concentrated. The obtained amorphous compound (487 mg) was dissolved in ethanol (2 mL) and tetrahydrofuran (2 mL), 1N lithium hydroxide (2.0 mL) was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (20 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (454 mg, 89%).

Workup

  1. washeluted with ethanol-hexane (1:1, volume ratio) as mobile phase at 30° C.
  2. customwere collected
  3. concentrationconcentrated
  4. dissolutionThe obtained amorphous compound (487 mg) was dissolved in ethanol (2 mL)
  5. additiontetrahydrofuran (2 mL), 1N lithium hydroxide (2.0 mL) was added
  6. customThe solvent was evaporated under reduced pressure, and water (20 mL)
  7. additionwas added
  8. temperaturecooling
  9. stirringstirred for 1 hr
  10. filtrationThe resulting precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-59491bf494c6453aa0b4eaa7d635b9ab
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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