Toluene → HCID 59370775, compound

HRID 1678722Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH2:9]I)=[CH:4][C:3]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].[CH2:24]([NH:31][CH2:32][CH2:33][OH:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(C)C=CC=CC=1>CCOCC>[CH2:24]([N:31]([CH2:32][CH2:33][OH:34])[CH2:9][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:4]=1)[O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(R)-N-(2-chloro-5-(2-iodo-1-(triethylsilyloxy)ethyl)phenyl)methanesulfonamide (3 g) and 2-(benzylamino)ethanol (6 mL; manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed, and the mixture was stirred overnight at 100° C. The reaction solution was cooled to room temperature, and then toluene and Et2O were added thereto. The mixture was washed three times with water, and the organic layer was dried over magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=84:16→64:36), and thus the title compound (2.1894 g) was obtained.

Workup

temperatureThe reaction solution was cooled to room temperature
washThe mixture was washed three times with water
dry with materialthe organic layer was dried over magnesium sulfate
customThen, the solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=84:16→64:36)

Sources & evidence

ORD record: ord-202e718141cf426db488aea094d95910
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008506B2

Reaction notes

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