Triethylamine → 3-Methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)azetidine

HRID 891734ノート

反応式

HRID 891734 の反応式
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][S:20]([O:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:7])[CH2:3]1)(=[O:22])=[O:21]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22242749(4-Nitrophenyl)methyl 3-hydroxyazetidine-1-carboxylate

生成物 1

HCID 222428573-Methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)azetidine収率 100.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-hydroxy-1-(p-nitrobenzyloxycarbonyl)azetidine (3.52 g, 14.0 mmol) (obtained as described in Reference Example 54(1)) in methylene chloride (106 ml) were added methanesulfonyl chloride (1.19 ml, 15.4 mmol) and triethylamine (2.16 ml, 15.4 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature overnight. After checking the completion of the reaction, 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 sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1→1:3) as the eluant to afford 3-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)-azetidine (4.63 g, yield 100%) as pale yellow crystals.

後処理

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-156d8f235be44e99a7333fa85c38d450
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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