Triethylamine → N-methoxy-N-methyl-3-oxocyclobutanecarboxamide

HRID 707350노트

반응식

HRID 707350 반응식
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.Cl.[CH3:10][O:11][NH:12][CH3:13].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.O>[CH3:10][O:11][N:12]([CH3:13])[C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 49133583-Oxocyclobutane-1-carboxylic acid

생성물 1

HCID 86634348N-methoxy-N-methyl-3-oxocyclobutanecarboxamide수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-oxo-cyclobutanecarboxylic acid (2.28 g, 20.0 mmol), O,N-dimethyl-hydroxylamine hydrochloride (1.94 g, 20.0 mmol), 1-hydroxybenzotriazole (2.99 g, 22.0 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (4.22 g, 22.0 mmol) and triethylamine (4.04 g, 40.0 mmol) in dichloromethane (50 mL) was stirred at room temperature for 24 hours. The mixture was diluted with water (30 mL), and extracted with dichloromethane (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), and dried over sodium sulfate. The filtrate was evaporated in vacuo and the residue was purified by silica chromatography to provide N-methoxy-N-methyl-3-oxocyclobutanecarboxamide (2.68 g, 17.0 mmol, yield: 85%).

후처리

  1. extractionextracted with dichloromethane (2×30 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-f645a08471ea44f3b558b89226ec050e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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