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

HRID 1966163ノート

反応式

HRID 1966163 の反応式
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]

参加物

7

反応物 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

生成物 1

HCID 86634348N-methoxy-N-methyl-3-oxocyclobutanecarboxamide収率 78.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6ee72202622449d5901311f3391f3cb6
出典データセット
uspto-grants-2013_04
特許番号
US08420629B2

反応ノート

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