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3-Fluorobenzothiohydrazide → Tert-butyl 3-(5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)butylcarbamate

HRID 512883
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HRID 512883 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=[S:8])[NH:6][NH2:7].[CH3:12][CH:13]([C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>C(O)C.C(Cl)Cl.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[S:8][C:24]([CH:13]([CH3:12])[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:7][N:6]=2)[CH:9]=[CH:10][CH:11]=1
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참가 물질

5

반응물 2

HCID 552816163-FluorobenzothiohydrazideHCID 67214951Tert-butyl 3-methyl-4-oxo-4-phenylbutylcarbamate

생성물 1

HCID 67215287Tert-butyl 3-(5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)butylcarbamate수율 48.4%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 21584144Dichloromethane ethanol용매

실험 절차

To a solution of 3-fluorobenzothiohydrazide (300 mg, 1.76 mmol) in ethanol/DCM (6 mL/2 mL) was added tert-butyl 3-methyl-4-oxo-4-phenylbutylcarbamate (538 mg, 1.94 mmol). After stirring at room temperature for 16 hours, acetic acid (3 drops) was added and the mixture stirred for another 48 hours. The reaction mixture was then concentrated under reduced pressure and chromatographed (9:1 hexanes/ethyl acetate) to provide the product (366 mg, 48%) as a mixture of diastereomers as a yellow foam.

후처리

  1. stirringthe mixture stirred for another 48 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customchromatographed (9:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-fd640207773c4844a33bf63944fd886d
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102639B2

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