Toluene → HCID 59370775, compound

HRID 1873975Notes

Reaction equation

HRID 1873975 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

5

Reactant 3

HCID 1140TolueneHCID 4348BenzylethanolamineHCID 53922285HCID 53922285, compound

Product 1

HCID 59370775HCID 59370775, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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; Tokyo Chemical Industry, Co., Ltd.) were admixed with each other and stirred overnight at 100° C. The reaction solution was cooled to room temperature, added with toluene and Et2O, and then washed with water three times. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=84:16→64:36) to obtain the title compound (2.1894 g).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washwashed with water three times
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=84:16→64:36)

Sources & evidence

ORD record
ord-1a01be00f86d4cb0b42a4c69e52e6de8
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

Loading…