Water → HCID 86651840, compound

HRID 1465449Notes

Reaction equation

HRID 1465449 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)[N:6]=1.C(N(CC)C(C)C)(C)C.[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30].O>C(Cl)(Cl)Cl>[CH2:29]([S:31]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)[N:6]=1)(=[O:33])=[O:32])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58181233HCID 58181233, compound

Product 1

HCID 86651840HCID 86651840, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl {4-[2-(2-amino-1,3-thiazol-4-yl)ethyl]phenyl}acetate (2.00 g, 7.24 mmol) in chloroform (20 ml) was added N,N-diisopropylethylamine (6.3 ml, 36.2 mmol), and the mixture was cooled to 0° C. Ethanesulfonyl chloride (0.82 ml, 8.7 mmol) was added dropwise, and the mixture was stirred at 0° C. overnight. Iced water (40 ml) was added to the reaction mixture, and the mixture was stirred for 10 mins. The mixture was extracted with ethyl acetate, and the combined organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1→1:0) to give methyl [4-(2-{2-[(ethylsulfonyl)amino]-1,3-thiazol-4-yl}ethyl)phenyl]acetate (1.76 g, yield 66%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 10 mins
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1→1:0)

Sources & evidence

ORD record
ord-503ed3b8ab5b4af7be343a8865089fab
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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