HCID 68507600, compound → HCID 42610135, compound

HRID 1877013Notes

Reaction equation

HRID 1877013 reaction equation
[CH:1]1([CH:7]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([N:34]([CH3:42])[CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[O:33])=[CH:28][CH:27]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[O:10][C:9]=2[CH2:23][CH3:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.CCCCCC>[CH:1]1([CH:7]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([N:34]([CH3:42])[CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:30][CH:31]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)[O:10][C:9]=2[CH2:23][CH3:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 68507600HCID 68507600, compound

Product 1

HCID 42610135HCID 42610135, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

Ethyl 3-[({4-[(cyclohexyl{2-ethyl-5-[4-(trifluoromethyl)phenyl]furan-3-yl}methyl)amino]phenyl}carbonyl)(methyl)amino]propanoate (880 mg) which is a synthetic intermediate in Example 10 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 were collected, and concentrated. The obtained amorphous compound (359 mg) was dissolved in ethanol (5 mL) and tetrahydrofuran (5 mL), 1N lithium hydroxide (2 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 (330 mg, 97%).

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 (359 mg) was dissolved in ethanol (5 mL)
  5. additiontetrahydrofuran (5 mL), 1N lithium hydroxide (2 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-879c1482bbd440fa9324b2544130674b
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

Loading…