Methanol → 1-(4-Cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

HRID 891558ノート

反応式

HRID 891558 の反応式
[C:1]([C:3]1[N:4]=[C:5]([N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[S:6][CH:7]=1)#[N:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.CO>C(Cl)Cl>[C:1]([C:3]1[N:4]=[C:5]([N:8]2[CH2:11][CH:10]([O:12][S:14]([CH3:13])(=[O:16])=[O:15])[CH2:9]2)[S:6][CH:7]=1)#[N:2]

参加物

6

反応物 4

HCID 887MethanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222427171-(4-Cyano-1,3-thiazol-2-yl)-3-hydroxyazetidine

生成物 1

HCID 222428691-(4-Cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine収率 100.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(4-cyano-1,3-thiazol-2-yl)-3-hydroxyazetidine (0.78 g, 4.3 mmol) (obtained as described in Reference Example 4(2)) in methylene chloride (40 ml) were added methanesulfonyl chloride (1.0 ml, 12.9 mmol) and triethylamine (1.8 ml, 12.9 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 40 minutes. After checking the completion of the reaction, methanol was added to the reaction mixture in an ice bath and then the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:ethyl acetate (1:1) as the eluant to afford 1-(4-cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (1.12 g, yield 100%) as a white solid.

後処理

  1. additionwas added to the reaction mixture in an ice bath
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-dc39905846214bc78efe6d61a9d24d56
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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