Potassium Carbonate → HCID 90177866, compound

HRID 1499308Notes

Reaction equation

HRID 1499308 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([S:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2].Br[CH2:37][CH2:38][CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.CCOCC>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([S:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:37][CH2:38][CH2:39][O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 90177023HCID 90177023, compound

Product 1

HCID 90177866HCID 90177866, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

(2S,3S,4R,5S,6R)-2-(3-(4-hydroxybenzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (37, 2.01 g, 4.0 mmol), ((3-bromopropoxy)methyl)benzene (1.41 mL, 8.0 mmol), Bu4NI (148 mg, 0.40 mmol), and K2CO3 (2.76 g, 20 mmol) were combined in DMF (8 mL) under nitrogen and stirred overnight at room temperature. The reaction was diluted with Et2O, washed with saturated aqueous NaHCO3 and brine (with back extraction), dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (gradient 0-50% EtOAc/hexanes) to give alkylated product 47 as a glassy solid (2.36 g, 91% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.28-7.36 (m, 5 H), 7.10-7.18 (m, 2 H), 7.03 (s, 1 H), 6.97 (d, J=8.6 Hz, 2 H), 6.77-6.84 (m, 2 H), 5.33 (t, J=9.6 Hz, 1 H), 5.21 (t, J=9.6 Hz, 1 H), 5.12 (t, J=9.6 Hz, 1 H), 4.48-4.54 (m, 3 H), 4.38 (d, J=9.9 Hz, 1 H), 4.06 (t, J=6.3 Hz, 2 H), 3.83-3.96 (m, 2H), 3.66 (t, J=6.2 Hz, 2 H), 2.21 (s, 3 H), 2.17 (s, 3 H), 2.10 (s, 3H) 2.04-2.12 (m, 2 H), 2.01 (s, 3 H), 1.75 (s, 3 H); MS (ES+) [M+NH4]+=668.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine (with back extraction)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel chromatography (gradient 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-86b209eae1e94fae9e90bb95402dda71
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Reaction notes

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