Potassium Carbonate → HCID 66632536, compound

HRID 1397193Notes

Reaction equation

HRID 1397193 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13][CH:14]1[CH:19]([C:20](=O)[NH:21][CH:22]([C:25](=[O:36])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][OH:24])[CH:18]2[O:38][CH:15]1[CH2:16][CH2:17]2.CCN(S(F)(F)F)CC.C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13][CH:14]1[CH:19]([C:20]2[O:24][CH2:23][CH:22]([C:25](=[O:36])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[N:21]=2)[CH:18]2[O:38][CH:15]1[CH2:16][CH2:17]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 66632736HCID 66632736, compound

Product 1

HCID 66632536HCID 66632536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{4-Fluoro-2-[3-(2-hydroxy-1-nonylcarbamoyl-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester (14.86 mmol) in dichloromethane (200 ml), at −78° C. and under nitrogen atmosphere, DAST (3.93 mL, 29.72 mmol) was added and the resulting mixture was stirred at room temperature for 2.5 h. After this time, potassium carbonate (4.11 g, 29.72 mmol) was added and the solution was stirred for another hour. Then saturated solution of NaHCO3 (200 mL) was added and the mixture was extracted with ethyl acetate (200 mL). Then, it was washed with Brine (150 mL), and dried over MgSO4. Filtration and concentrated in vacuo yield the crude compound as thick oil.

Workup

  1. stirringthe solution was stirred for another hour
  2. extractionthe mixture was extracted with ethyl acetate (200 mL)
  3. washThen, it was washed with Brine (150 mL)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5705e16198c24a308b0c9155bc4c6251
Source dataset
uspto-grants-2014_12
Patent number
US08901159B2

Reaction notes

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