Methanol → HCID 68504143, compound

HRID 1712571Notes

Reaction equation

HRID 1712571 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH:31]5[CH2:34][N:33]([C:35]6[S:36][CH:37]=[CH:38][N:39]=6)[CH2:32]5)=[CH:26][CH:25]=4)[CH2:22][CH2:21][N:20](C(OCC4C=CC=CC=4)=O)[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1.CO.[OH-].[K+]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH:31]5[CH2:32][N:33]([C:35]6[S:36][CH:37]=[CH:38][N:39]=6)[CH2:34]5)=[CH:26][CH:25]=4)[CH2:22][CH2:21][NH:20][CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68497856HCID 68497856, compound

Product 1

HCID 68504143HCID 68504143, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

0.190 g of benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benz[1,4]oxazin-6-ylmethoxy]-4-[4-(1-thiazol-2-ylazetidin-3-yloxy)phenyl]piperidinecarboxylate is dissolved in 8 ml of dioxane. 8 ml each of methanol and 40% KOH are added and the reaction mixture is stirred at 100° C. in a sealed flask over 5 hours. The reaction mixture is subsequently cooled to room temperature, diluted with 40 ml of water and extracted with ethyl acetate (3×40 ml). The combined organic phases are washed with 40 ml of water, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. temperatureThe reaction mixture is subsequently cooled to room temperature
  2. extractionextracted with ethyl acetate (3×40 ml)
  3. washThe combined organic phases are washed with 40 ml of water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3f7e1f71881f42289c5510c4ca60903a
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

Loading…