Ethylene Glycol → HCID 90828874, compound
Reaction equation
[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:32])([CH2:21][CH2:22][C@@H:23]([O:27]S(C)(=O)=O)[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:34])([C@@H:17]([OH:33])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1.[CH2:35](O)[CH2:36][OH:37].N1C=CC=CC=1>CCOC(C)=O>[OH:1][C@@H:2]1[CH2:26][C@@H:25]2[C@:20]([CH3:32])([CH2:21][CH2:22][C@H:23]([O:27][CH2:35][CH2:36][OH:37])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:34])([C@@H:17]([OH:33])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 HCI (30 mL). The layers were separated and the organic layer was washed with 1N HCI (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
- customsealed
- temperatureThe reaction was cooled to ambient temperature
- customquenched with 1N HCI (30 mL)
- customThe layers were separated
- washthe organic layer was washed with 1N HCI (2×30 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customPurification by silica gel chromatography (10%->40% acetone/hexanes)
Sources & evidence
- ORD record
- ord-db192792345a4c79b5b185e25eeb8b9a
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07521439B2
Reaction notes
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