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

HRID 1966163노트

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HRID 1966163 반응식
Cl.[CH3:2][NH:3][O:4][CH3:5].[O:6]=[C:7]1[CH2:10][CH:9]([C:11]([OH:13])=O)[CH2:8]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH3:5][O:4][N:3]([CH3:2])[C:11]([CH:9]1[CH2:8][C:7](=[O:6])[CH2:10]1)=[O:13]

참가 물질

7

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 78.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of N,O-dimethylhydroxylamine hydrochloride (5.2 g, 0.054 mol), and 3-oxocyclobutanecarboxylic acid (4.0 g, 0.035 mol) in dichloromethane (30 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.0 g, 0.052 mol), 1-hydroxybenzotriazole (7.1 g, 0.052 mol) followed by triethylamine (34 mL, 0.24 mol) at 0° C. The mixture was stirred at rt over night, then quenched with water. The mixture was extracted with EtOAc. The organic layers were dried over MgSO4, concentrated and purified with Combiflash (silica gel, 0-5% for 30 min followed by 5-20% EtOAc/Hex) to give the desired product (4.3 g, 78%) as light yellow oil. LCMS calculated for C7H12NO3(M+H)+: 158.1. Found: 158.3.

후처리

  1. customquenched with water
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified with Combiflash (silica gel, 0-5% for 30 min followed by 5-20% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-6ee72202622449d5901311f3391f3cb6
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420629B2

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