Isopropyl iodide → HCID 68752508, compound

HRID 573526Notes

Reaction equation

[CH3:1][Si:2]([CH3:32])([C:28]([CH3:31])([CH3:30])[CH3:29])[O:3][CH2:4][C@@H:5]1[C@@H:14]2[C@@H:8]([O:9][CH2:10][C:11]([CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][CH2:13]2)[CH2:7][C@H:6]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1.C(=O)([O-])[O-].[K+].[K+].[CH:39](I)([CH3:41])[CH3:40].CC(OC)(C)C>CN(C=O)C.O>[CH3:32][Si:2]([CH3:1])([C:28]([CH3:29])([CH3:31])[CH3:30])[O:3][CH2:4][C@@H:5]1[C@@H:14]2[C@@H:8]([O:9][CH2:10][C:11]([CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:39]([CH3:41])[CH3:40])=[O:19])=[CH:12][CH2:13]2)[CH2:7][C@H:6]1[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

Under the argon atmosphere, the compound (15.4 mmol) produced in Example 7 was dissolved in DMF; potassium carbonate (5.31 g, 38.5 mmol) and isopropyl iodide (2.31 mL, 23.1 mmol) were added, followed by stirring at 60° C. for 3 hours. After cooling, MTBE and water were added, and extraction; washing with a saturated saline; drying with anhydrous sodium sulfate; and concentration were carried out. Purification by silica gel column chromatography (hexane:ethyl acetate=90:10→50:50) was carried out to obtain a titled compound (7.25 g) having the following physical property values.

Workup

temperatureAfter cooling
extractionextraction
washwashing with a saturated saline
dry with materialdrying with anhydrous sodium sulfate
concentrationand concentration
customPurification by silica gel column chromatography (hexane:ethyl acetate=90:10→50:50)

Sources & evidence

ORD record: ord-61378f0a0f284886b7d8ff9eb007c54a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029574B2

Reaction notes

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