Diisopropylethylamine → 4-methyl-N-((1S,2S)-2-(4-(5-methylcyclohexa-1,4-dienyl)buty lamino)-1,2-diphenylethyl)benzenesulfonamide

HRID 878932Notes

Reaction equation

CCN([CH:7]([CH3:9])[CH3:8])C(C)C.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C@H:21]([C@@H:28]([NH2:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C@@H:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:28]([NH:35][CH2:31][CH2:30][CH2:29][CH2:28][C:21]2[CH2:9][C:7]([CH3:8])=[CH:24][CH2:23][CH:22]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 135 °C

Procedure

The tosylates (10.45 g, 32.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 2 were dissolved in 40 ml of toluene, and DIPEA (4.79 g, 32.61 mmol) and (S,S)-TsDPEN (11.95 g, 32.61 mmol) were added thereto, followed by stirring at 135° C. for 14 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 9.31 g of the title compounds were obtained as a yellow oily substance. Yield: 55.5% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture.

Workup

customAfter that, the solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-9d73f40b6ed84ee2a8e9a0b1db8c2de4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987492B2

Reaction notes

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