Potassium Carbonate → HCID 57718998, compound

HRID 1985122Notes

Reaction equation

[C:1]([C:5]1[CH:29]=[CH:28][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[CH:19]=3)[N:12]([CH3:26])[C:11]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:31]([CH3:38])([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:35]([O:34][C:32](=[O:33])[C:31]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][CH2:15][CH:13]2[CH2:14][N:10]([CH2:9][C:8]3[CH:28]=[CH:29][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=3)[C:11](=[O:27])[N:12]2[CH3:26])=[CH:19][C:20]=1[CH3:25])([CH3:38])[CH3:37])[CH3:36]

Participants

Conditions

Temperature: 50 °C

Procedure

1-(4-tert-Butyl-benzyl)-4-[3-(4-hydroxy-3-methyl-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.060 g, 0.152 mmol) is dissolved in DMF (1.5 mL), to it is added ethyl 2-bromoisobutyrate (0.141 g, 0.760 mmol) followed by potassium carbonate (0.105 g, 0.760 mmol). After heating at 50° C. overnight, the reaction mixture is diluted with ethyl acetate (2 mL), washed with water (2 mL), the separated organic layer is passed through a chem elut tube, and the tube is washed with more DCM (50 mL). Evaporation of solvent followed by chromatography on silica gel, (gradient elution 0-40% ethyl acetate in hexane) to provide an oil (0.068 g, 88%). Mass [EI+] 510 (M+H)+.

Workup

washwashed with water (2 mL)
customthe separated organic layer is passed through a chem elut tube
washthe tube is washed with more DCM (50 mL)
customEvaporation of solvent
washfollowed by chromatography on silica gel, (gradient elution 0-40% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-a1f65554570244f5bbffc07d347e2b1a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544812B2

Reaction notes

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