HCID 67166124, compound → HCID 67164705, compound

HRID 553308Notes

Reaction equation

HRID 553308 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][O:17]C2CCCCO2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CC(O)=O.O>[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][OH:17])[CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 1

HCID 67166124HCID 67166124, compound

Product 1

HCID 67164705HCID 67164705, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2-Methoxy-benzyl)-{3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzyl}-carbamic acid tert-butyl ester (51 g) was dissolved in a mixture of THF (250 mL), AcOH (225 mL) and water (150 mL) and the resulting mixture refluxed for a total of 10 hours. The majority of the tetrahydrofuran and acetic acid was evaporated and the pH of was adjusted to 8 using saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with ethyl acetate (3×250 mL) and the combined organics were washed with water (250 mL), brine (250 mL), dried over sodium sulfate, filtered and evaporated. The crude material was purified in two portions by column chromatography eluting with dichloromethane:ethyl acetate (95:5 to 80:20 gradient) to give a yellow oil (total of 17.2 g).

Workup

  1. temperaturethe resulting mixture refluxed for a total of 10 hours
  2. customThe majority of the tetrahydrofuran and acetic acid was evaporated
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×250 mL)
  4. washthe combined organics were washed with water (250 mL), brine (250 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material was purified in two portions by column chromatography
  9. washeluting with dichloromethane:ethyl acetate (95:5 to 80:20 gradient)
  10. customto give a yellow oil (total of 17.2 g)

Sources & evidence

ORD record
ord-f6fa1044846b46d8aff0aaba970a740e
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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