Triethylamine → HCID 89853822, 화합물

HRID 931112노트

반응식

HRID 931112 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 89853822HCID 89853822, 화합물수율 83%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ccf760384c144c1c9205920d570f1e23
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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