Cesium carbonate → 5-(4-Methoxy-3-(2-(2-((2-methyladamantan-2-yl)oxy)-2-oxoethoxy)-2-oxoethyl)phenyl)-dibenzothiophenium chloride

HRID 625182Notes

Reaction equation

HRID 625182 reaction equation
[I-].[C:2]([CH2:5][C:6]1[CH:7]=[C:8]([S+:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[CH:23]=[CH:24][CH:25]=[CH:26][C:15]2=3)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])([OH:4])=[O:3].[Cl:27][CH2:28][C:29]([O:31][C:32]1([CH3:42])[CH:39]2[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:41][CH:33]1[CH2:34]3)[CH2:38]2)=[O:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl-:27].[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([S+:14]2[C:15]3[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]2=3)=[CH:7][C:6]=1[CH2:5][C:2]([O:4][CH2:28][C:29]([O:31][C:32]1([CH3:42])[CH:39]2[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:41][CH:33]1[CH2:34]3)[CH2:38]2)=[O:30])=[O:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 103320062-Methyl-2-adamantyl chloroacetateHCID 131735197HCID 131735197, compound

Product 1

HCID 1317351955-(4-Methoxy-3-(2-(2-((2-methyladamantan-2-yl)oxy)-2-oxoethoxy)-2-oxoethyl)phenyl)-dibenzothiophenium chlorideYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

5-(3-(carboxymethyl)-4-methoxyphenyl)-dibenzothiophenium iodide (15.0 g, 31.5 mmol) was dissolved in DMF (100 mL) and degassed with nitrogen for 30 min, then 2-methyladamantan-2-yl 2-chloroacetate (7.49 g, 31.0 mmol) and cesium carbonate (14.4 g, 44.1 mmol) were added sequentially and the mixture stirred at 25° C. for 6 h. The solution was diluted with water (200 mL), extracted with DCM (2×150 mL), the combined organic layers washed with water (5×150 mL) and concentrated to a viscous oil which was poured onto MTBE (1 L) and vigorously stirred for 1 h. The precipitate was filtered, washed with MTBE (2×250 mL) and dried to afford the title compound (18.2 g, 99%) as a white solid. 1H NMR (300 MHz, (CD3)2SO) δ: 8.51 (d, J=8.1 Hz, 2H), 8.29 (d, J=8.1 Hz, 2H), 7.95 (t, J=7.5 Hz, 2H), 7.70-7.81 (m, 3H), 7.32 (d, J=2.1 Hz, 1H), 7.25 (dd, J=7.5, 2.1 Hz, 1H), 4.56 (s, 2H), 3.82 (s, 3H), 3.65 (s, 2H), 2.10-2.19 (m, 2H), 1.61-1.95 (m, 11H), 1.52 (s, 3H), 1.39-1.50 (m, 2H).

Workup

  1. customdegassed with nitrogen for 30 min
  2. extractionextracted with DCM (2×150 mL)
  3. washthe combined organic layers washed with water (5×150 mL)
  4. concentrationconcentrated to a viscous oil which
  5. additionwas poured onto MTBE (1 L)
  6. stirringvigorously stirred for 1 h
  7. filtrationThe precipitate was filtered
  8. washwashed with MTBE (2×250 mL)
  9. customdried

Sources & evidence

ORD record
ord-9f788dad5d7b4dba8536321cd3df743a
Source dataset
uspto-grants-2016_04
Patent number
US09304394B2

Reaction notes

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