2-Aminophenol → Methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate

HRID 2241356ノート

反応式

HRID 2241356 の反応式
[CH3:1][O:2][C:3]([C:5]1([C:8]([O-:10])=O)[CH2:7][CH2:6]1)=[O:4].[K+].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34]>C1COCC1.C(OCC)(=O)C.CN(C=O)C>[OH:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[NH:27][C:8]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]1)=[O:10]

参加物

8

反応物 4

HCID 58012-AminophenolHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 68516896Potassium 1-(methoxycarbonyl)cyclopropanecarboxylate

生成物 1

HCID 68513898Methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate収率 68%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred suspension of potassium 1-(methoxycarbonyl)cyclopropanecarboxylate (182 mg, 1 mmol) in 3 mL THF at room temperature under nitrogen was added 15 μL of DMF. Oxalyl chloride (87 μL, 1 mmol) was then added neat dropwise by syringe. After stirring at ambient temperature for 2 hours, the reaction was cooled to 0° C. and treated with DIEA (0.497 ml, 2.85 mmol) followed by 2-aminophenol (104 mg, 0.951 mmol) neat as a solid. The cooling bath was allowed to melt and the reaction was then stirred at ambient temperature overnight. The reaction was diluted to 30 mL with ethyl acetate and washed with 2N HCl, water, saturated sodium bicarbonate and brine. The organics were dried (MgSO4), filtered and concentrated to a yellow solid (147 mg, 68% yield).

後処理

  1. temperaturethe reaction was cooled to 0° C.
  2. stirringthe reaction was then stirred at ambient temperature overnight
  3. washwashed with 2N HCl, water, saturated sodium bicarbonate and brine
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-0dab543180ec49db89f37c8404b3c26c
出典データセット
uspto-grants-2010_05
特許番号
US07723330B2

反応ノート

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