HCID 60077679, compound → HCID 60077668, compound

HRID 1350211Notes

Reaction equation

HRID 1350211 reaction equation
C([N:14]1[CH2:17][CH:16]([C:18]2[N:22]=[C:21]([C@H:23]([CH2:32][CH2:33][CH2:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH2:24][C:25]([O:27][C:28](C)(C)C)=[O:26])[O:20][N:19]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[NH:14]1[CH2:17][CH:16]([C:18]2[N:22]=[C:21]([C@H:23]([CH2:32][CH2:33][CH2:34][CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[CH2:24][C:25]([O:27][CH3:28])=[O:26])[O:20][N:19]=2)[CH2:15]1

Participants

3

Reactant 1

HCID 60077679HCID 60077679, compound

Product 1

HCID 60077668HCID 60077668, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(3R)-3-[3-(1-benzhydryl-3-azetidinyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 36) (1.99 g, 3.66 mmol) in DCM (15 ml) was treated with ACE-CI (530 μl, 4.90 mmol) and heated at reflux for 4 hours. The solvent was removed under reduced pressure. The residue was dissolved in MeOH (15 ml) and heated at reflux for 1.5 hours. The solvent was removed under reduced pressure. The oil was dissolved in EtOAc (150 ml) and washed with sat. NaHCO3 solution (50 ml) and brine (40 ml). The aqueous extracts were combined and extracted with EtOAc. All of the organic extracts were combined, dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure to afford the title compound as a colourless oil (900 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in MeOH (15 ml)
  5. temperatureheated
  6. temperatureat reflux for 1.5 hours
  7. customThe solvent was removed under reduced pressure
  8. dissolutionThe oil was dissolved in EtOAc (150 ml)
  9. washwashed with sat. NaHCO3 solution (50 ml) and brine (40 ml)
  10. extractionextracted with EtOAc
  11. dry with materialdried over anhydrous Na2SO4
  12. filtrationfiltered
  13. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-edd9ffa13ea34c3cb9aa69d865e61fa8
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

Loading…