Potassium Carbonate → HCID 11950364, compound

HRID 251446Notes

Reaction equation

HRID 251446 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:26]=[CH:25][C:14]([C:15]([NH:17][C@H:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][OH:20])=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(S(F)(F)F)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:26]=[CH:25][C:14]([C:15]3[O:20][CH2:19][CH:18]([C:21]([O:23][CH3:24])=[O:22])[N:17]=3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 11950363HCID 11950363, compound

Product 1

HCID 11950364HCID 11950364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl N-[4-(3-piperidin-1-ylpropoxy)benzoyl]serinate ax37 (0.922 g, 2.54 mmol, 1 eq) and (diethylamino)sulfur trifluoride (0.34 ml, 2.78 mmol, 1.1 eq) in dichloromethane (25 ml) is stirred under argon at room temperature for 3.5 h before addition of potassium carbonate (0.35 g, 2.53 mmol, 1 eq). The mixture is stirred for a further 1 h and washed with a saturated solution of potassium hydrogencarbonate and the aqueous layer is extracted with dichloromethane. The organic layers are then dried over magnesium sulfate and concentrated under vacuum to give methyl 2-[4-(3-piperidin-1-ylpropoxy)phenyl]-4,5-dihydro-1,3-oxazole-4-carboxylate ax45 as an orange oil (1.036 g) which is used without further purification.

Workup

  1. washwashed with a saturated solution of potassium hydrogencarbonate
  2. extractionthe aqueous layer is extracted with dichloromethane
  3. dry with materialThe organic layers are then dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-21f665d805df45c8b1b1e3c9d53f9551
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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