HCID 68512728, compound → HCID 59529323, compound

HRID 1877115Notes

Reaction equation

HRID 1877115 reaction equation
[CH3:1][N:2]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH:19]([C:24]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:25]=2[CH3:35])[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:14][CH:13]=1)=[O:11])[CH2:3][CH2:4][C:5]([O:7]CC)=[O:6]>C(O)C.CCCCCC>[CH3:1][N:2]([C:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH:19]([C:24]2[CH:28]=[C:27]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[O:26][C:25]=2[CH3:35])[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=1)=[O:11])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 68512728HCID 68512728, compound

Product 1

HCID 59529323HCID 59529323, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

Ethyl 3-{methyl[(4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoate (2.54 g) which is a synthetic intermediate in Example 125 was dissolved in ethanol-hexane (1:1, volume ratio), and the solution was subjected to HPLC using CHIRALPAK AD (50 mmID×500 mL, 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 12 min was collected, and concentrated. The obtained amorphous compound (1.24 g) was dissolved in ethanol (5 mL) and tetrahydrofuran (5 mL), 1N lithium hydroxide (5.5 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 (1.1 g, 97%).

Workup

  1. washeluted with ethanol-hexane (1:1, volume ratio) as mobile phase at 30° C.
  2. customwas collected
  3. concentrationconcentrated
  4. dissolutionThe obtained amorphous compound (1.24 g) was dissolved in ethanol (5 mL)
  5. additiontetrahydrofuran (5 mL), 1N lithium hydroxide (5.5 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-5be8c26106b14a5aabcf7b85541e73b6
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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