Sodium Iodide → 5-(4-Methoxy-3-(2-oxo-2-(2-oxo-2-(2-oxo-2-((2-phenylpropan-2-yl)oxy)ethoxy)ethoxy)ethyl)phenyl)-dibenzothiophenium chloride

HRID 625185Notes

Reaction equation

[Cl-:1].[C:2]([CH2:5][O:6][C:7](=[O:30])[CH2:8][C:9]1[CH:10]=[C:11]([S+:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:19]3[CH:26]=[CH:27][CH:28]=[CH:29][C:18]2=3)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])([OH:4])=[O:3].Br[CH2:32][C:33]([O:35][C:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([CH3:38])[CH3:37])=[O:34].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl-:1].[CH3:16][O:15][C:14]1[CH:13]=[CH:12][C:11]([S+:17]2[C:18]3[CH:29]=[CH:28][CH:27]=[CH:26][C:19]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]2=3)=[CH:10][C:9]=1[CH2:8][C:7](=[O:30])[O:6][CH2:5][C:2](=[O:4])[O:3][CH2:32][C:33](=[O:34])[O:35][C:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([CH3:37])[CH3:38]

Participants

Conditions

Temperature: 25 °C

Procedure

5-(3-(2-(carboxymethoxy)-2-oxoethyl)-4-methoxyphenyl)dibenzothiophenium chloride (25 g, 59.2 mmol), 2-phenylpropan-2-yl 2-bromoacetate (15.2 g, 59.2 mmol), sodium iodide (17.7 g, 0.118 mmol), and cesium carbonate (38.4 g, 0.118 mmol) are dissolved in DMF (200 mL) and stirred at 25° C. for 4 h. The reaction mixture is quenched with water (500 mL), extracted with DCM (2×200 mL), the combined organic layers washed with water (4×200 mL), concentrated to a viscous oil and precipitated from MTBE (1 L) to afford the title compound as a white solid.

Workup

customThe reaction mixture is quenched with water (500 mL)
extractionextracted with DCM (2×200 mL)
washthe combined organic layers washed with water (4×200 mL)
concentrationconcentrated to a viscous oil
customprecipitated from MTBE (1 L)

Sources & evidence

ORD record: ord-38a58a27cfd04c8fa7fa878dd634aa85
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09304394B2

Reaction notes

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