Potassium Carbonate → HCID 68504601, compound

HRID 1176456Notes

Reaction equation

HRID 1176456 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][CH:36]=[CH:35][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH:32]2[CH2:34][O:33]2)=[CH:13][CH:12]=1.[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[NH:46][S:47]([C:50]1[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=1)(=[O:49])=[O:48].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.Cl>[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[N:46]([S:47]([C:50]1[CH:51]=[CH:52][C:53]([CH3:56])=[CH:54][CH:55]=1)(=[O:48])=[O:49])[CH2:34][CH:32]([OH:33])[CH2:31][O:30][CH:18]1[CH:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]3[CH:35]=[CH:36][CH:37]=[CH:38][C:3]=3[O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 433294Lithium Chloride2×HCID 737603HCID 737603, compoundHCID 87475792HCID 87475792, compound

Product 1

HCID 68504601HCID 68504601, compound

Reagents, catalysts & solvents 3

HCID 165294Benzyltriethylammonium bromideCatalyst2×HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2.20 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-oxiranylmethoxypiperidine-1-carboxylate, 1.23 g of N-(2-fluorophenyl)-4-methylbenzenesulphonamide, 0.29 g of potassium carbonate, 0.35 g of benzyltriethylammonium bromide and 0.053 g of lithium chloride in 30 ml of dioxane is stirred at 90° C. over 17 hours. After 18 hours, another 0.20 g of lithium chloride, 0.50 g of potassium carbonate and 0.30 g of benzyltriethylammonium bromide are added. After a total of 40 hours, the reaction mixture is cooled to room temperature, diluted with 1N HCl and extracted with tert-butyl methyl ether (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.14 (1:2 EtOAc-heptane); Rt=5.96.

Workup

  1. waitAfter 18 hours
  2. temperatureAfter a total of 40 hours, the reaction mixture is cooled to room temperature
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-856676a697114faeb29533c66086f032
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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