Triethylamine → HCID 89853822、化合物

HRID 931112ノート

反応式

HRID 931112 の反応式
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=2)[CH2:3][CH2:2]1.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[CH3:33][NH:34][O:35][CH3:36].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([N:34]([O:35][CH3:36])[CH3:33])=[O:11])[N:8]=2)[CH2:2][CH2:3]1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 252192732-Cyclopropyl-1,3-oxazole-4-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 89853822HCID 89853822、化合物収率 83%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-cyclopropyloxazole-4-carboxylic acid (0.1 g, 0.653 mmol) in dry dichloromethane (15 mL) were added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.25 g, 1.3 mmol) and hydroxybenzotriazole (0.175 g, 1.3 mmol) at 0° C. portion wise. N,O-dimethylhydroxylamine (64 mg, 0.653 mmol) was then added followed by triethylamine (0.26 mL, 1.95 mmol). The reaction mixture was stirred at room temperature for 18 h then diluted with ethyl acetate and washed with water and brine solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified by preparative TLC (25% ethyl acetate in petroleum ether) to afford 2-cyclopropyl-N-methoxy-N-methyloxazole-4-carboxamide (100 mg, 83%). MS (ES+) (M+H) 197.25; LCMS retention time: 2.82 min (Method S).

後処理

  1. washwashed with water and brine solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by preparative TLC (25% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-ccf760384c144c1c9205920d570f1e23
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

読み込み中…