4-Methylcyclohexane-1-carbonyl chloride → 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester

HRID 1614914노트

반응식

HRID 1614914 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:19]#[C:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][P:13]([O:16][CH2:17][CH3:18])([CH3:15])=[O:14])=[O:4].[CH3:25][CH:26]1[CH2:31][CH2:30][CH:29]([C:32](Cl)=[O:33])[CH2:28][CH2:27]1>N1C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:19]#[C:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:8][C:9]=1[N:10]([CH2:11][CH2:12][P:13]([O:16][CH2:17][CH3:18])([CH3:15])=[O:14])[C:32]([CH:29]1[CH2:30][CH2:31][CH:26]([CH3:25])[CH2:27][CH2:28]1)=[O:33])=[O:4]

참가 물질

5

반응물 2

HCID 129863574-Methylcyclohexane-1-carbonyl chlorideHCID 670343375-(3,3-Dimethyl-but-1-ynyl)-3-[2-(ethoxy-methyl-phosphinoyl)-ethylamino]-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 670337505-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester수율 80.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

5-(3,3-Dimethyl-but-1-ynyl)-3-[2-(ethoxy-methyl-phosphinoyl)-ethylamino]-thiophene-2-carboxylic acid methyl ester (233 mg, 0.629 mmol) was dissolved in pyridine (4 mL) and then 4-methyl-cyclohexanecarbonyl chloride (506 mg, 3.15 mmol) was added. The reaction was stirred for 7 hours at 100° C., the heat to the oil bath was shut off and the reaction was allowed to stir for a further 9 hours. The reaction was diluted with EtOAc and extracted with H2O. The organic phase was then extracted with brine and dried over Na2SO4. The drying agent was removed by vacuum filtration and the filtrate was concentrated. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (251 mg, 78%) was isolated from the residue by silica gel column chromatography.

후처리

  1. temperaturethe heat to the oil bath
  2. stirringto stir for a further 9 hours
  3. extractionextracted with H2O
  4. extractionThe organic phase was then extracted with brine
  5. dry with materialdried over Na2SO4
  6. customThe drying agent was removed by vacuum filtration
  7. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-f3453c449dbe4886a96a657d349ed864
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765722B2

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