1,1'-Carbonyldiimidazole → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

HRID 1873852ノート

反応式

HRID 1873852 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl-].[CH3:28][O:29][NH2+:30][CH3:31].C(N(C(C)C)CC)(C)C>CCOCC.O1CCCC1>[CH3:28][O:29][N:30]([CH3:31])[C:12]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]1)=[O:14]

参加物

7

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 11040634Methoxy(methyl)azanium;chloride

生成物 1

HCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate収率 79.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a 100 ml round bottom flask was added 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (3.75 g, 18.6 mmol) and 20 ml tetrahydrofuran, followed by CDI (3.63 g, 22.4 mmol). Vigorous gas evolution was observed. After gas evolution stopped, the reaction mixture was stirred at room temperature for additional 30 minutes. Methoxy(methyl)ammonium chloride (2.55 g, 26.1 mmol) was added, followed by diisopropylethyl amine (6.5 ml, 37.3 mmol). The resulting reaction mixture was stirred at room temperature overnight. It was diluted with 120 ml ether and washed with 60 ml saturated NH4Cl. The organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel column, eluted with 1:2 to 3:2 ethyl acetate/hexane to give 3.6 g desired product was colorless oil.

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature overnight
  3. washwashed with 60 ml saturated NH4Cl
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel column
  8. washeluted with 1:2 to 3:2 ethyl acetate/hexane

出典と根拠

ORDレコード
ord-d8b6efe02de34818bbbe789cc411540e
出典データセット
uspto-grants-2012_11
特許番号
US08304434B2

反応ノート

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