Ethylene Glycol → HCID 15703127, compound

HRID 724542Notes

Reaction equation

HRID 724542 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@H:15]([CH2:16][C@@H:17]([O:28]S(C)(=O)=O)[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:33])[CH2:10][CH2:9]1)[CH3:7].[CH2:35](O)[CH2:36][OH:37].N1C=CC=CC=1>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:35][CH2:36][OH:37])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:33])[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1049PyridineHCID 87923788HCID 87923788, compound

Product 1

HCID 15703127HCID 15703127, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A pressure vessel (250 mL flask) containing the compound of Example 1A (10.0 g, 20 mmol) was charged with ethylene glycol (20 mL) and pyridine (4 mL) at ambient temperature, sealed and then heated at 120° C. for 4 hours. The reaction was cooled to ambient temperature, diluted with EtOAc (50 mL), and quenched with 1N HCl (30 mL). The layers were separated and the organic layer was washed with 1N HCl (2×30 mL), dried (Na2SO4), and concentrated. Purification by silica gel chromatography (10%—>40% acetone/hexanes) provided the title compound (3.5 g, 37%). MS (ESI) m/e 484 (M+NH4)+

Workup

  1. customsealed
  2. temperatureThe reaction was cooled to ambient temperature
  3. customquenched with 1N HCl (30 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with 1N HCl (2×30 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (10%—>40% acetone/hexanes)

Sources & evidence

ORD record
ord-c03e0e4a39c149ad81b04b3667021ee0
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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