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Triethylamine → (S)-3-phenethylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester

HRID 1668413
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HRID 1668413 반응식
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][NH:13]1)=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:25]([O:32][C:33]([N:14]1[CH2:15][CH2:16][CH2:17][C@@H:12]([C:10](=[O:11])[NH:9][CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:13]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 57612768(S)-hexahydro pyridazine-3-carboxylic acid phenethyl-amide

생성물 1

HCID 57612817(S)-3-phenethylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester수율 99.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-5 °C

실험 절차

To a solution of (S)-hexahydro pyridazine-3-carboxylic acid phenethyl-amide (376 mg, 1.59 mmol) and Et3N (0.66 mL) in CH2Cl2 (10 mL) at 0° C., is added benzylchloroformate (270 mg, 1.59 mmol) dropwise. After stirring at −5° C. for 1.5 hours, the reaction mixture is diluted with CH2Cl2 (50 mL) and washed with 10 mL of water. The organic layer is dried over Na2SO4 and concentrated to give (S)-3-phenethylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester (580 mg) as pale gum without further purification for next step reaction. (NMR and MS data confirmed, U-3133-59).

후처리

  1. washwashed with 10 mL of water
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-84db6e2e5d114ae698747ced9b59153a
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989441B2

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