HCID 55300025, compound → HCID 66875080, compound

HRID 249881Notes

Reaction equation

HRID 249881 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[CH2:15]([C@H:17]1[CH2:22][O:21][CH2:20][C@H:19]([CH3:23])[NH:18]1)[CH3:16]>C1COCC1>[CH2:15]([C@@H:17]1[N:18]([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)[C@@H:19]([CH3:23])[CH2:20][O:21][CH2:22]1)[CH3:16]

Participants

4

Reactant 2

HCID 55300025HCID 55300025, compoundHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66875080HCID 66875080, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (750 mg, 3.54 mmol) and (3S,5S)-3-ethyl-5-methylmorpholine (1.00 g, 7.75 mmol) in THF (40 mL) was stirred at ambient temperature overnight. Then the reaction mixture was heated in a 50° C. oil bath for 4.5 h. The reaction mixture was cooled to ambient temperature and most of the THF was removed under reduced pressure. The residue was dissolved in EtOAc (150 mL) and washed with 0.5 N HCl (25 ml), H2O (25 mL), brine (25 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, hexanes to 10% EtOAc in hexanes) to give methyl 2-((3S,5S)-3-ethyl-5-methylmorpholino)benzoxazole-4-carboxylate (540 mg, 50%), as a colorless oil. 1H NMR consistent.

Workup

  1. temperatureThen the reaction mixture was heated in a 50° C. oil bath for 4.5 h
  2. customwas removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (150 mL)
  4. washwashed with 0.5 N HCl (25 ml), H2O (25 mL), brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography (silica gel, hexanes to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-afbd9fc63dd748bcaaa98cb90eafdda2
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

Loading…