Dimethylformamide → HCID 60141379, compound

HRID 1746824Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[CH:7](I)([CH3:9])[CH3:8].CN(C)C=O.[OH:16][C@@H:17]1[CH2:31][C@@H:20]2[S:21][C@@H:22]([CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:23][CH2:24][C@@H:19]2[C@H:18]1/[CH:32]=[CH:33]/[C@@H:34]([OH:43])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(OCC)(=O)C>[OH:16][C@@H:17]1[CH2:31][C@@H:20]2[S:21][C@@H:22]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:7]([CH3:9])[CH3:8])=[O:29])[CH2:23][CH2:24][C@@H:19]2[C@H:18]1[CH2:32][CH2:33][C@@H:34]([OH:43])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Under the argon atmosphere, cesium carbonate (68 mg) and isopropyl iodide (0.016 mL) were added to a dimethylformamide (0.4 mL) solution of the compound 15 (20) (42.8 mg), and the mixture was stirred at 50° C. for 90 minutes. This was cooled to room temperature, ethyl acetate was then added, and the mixture was washed with water two times, and then with a saturated saline once. The mixture was dried with anhydrous magnesium sulfate, and then concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3→1:1) to obtain a titled compound (34 mg) having the following physical property values.

Workup

temperatureThis was cooled to room temperature
washthe mixture was washed with water two times
dry with materialThe mixture was dried with anhydrous magnesium sulfate
concentrationconcentrated
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3→1:1)

Sources & evidence

ORD record: ord-1bbc501a91c24a9b88ff77f8a69bcdaf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150537B2

Reaction notes

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