tert-Butyl carbazate → tert-butyl N'-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazinecarboxylate

HRID 1009348노트

반응식

HRID 1009348 반응식
C1C=CC2N(O)N=NC=2C=1.FC(F)(F)C(O)=O.[Cl:18][CH2:19][CH2:20][CH2:21]/[C:22](=[CH:26]\[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]2)=[C:29]([O:39][CH3:40])[CH:28]=1)/[C:23]([OH:25])=O.[C:41]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])(=[O:44])[NH:42][NH2:43].C(N(C(C)C)CC)(C)C.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[Cl:18][CH2:19][CH2:20][CH2:21]/[C:22](=[CH:26]\[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]2)=[C:29]([O:39][CH3:40])[CH:28]=1)/[C:23]([NH:43][NH:42][C:41]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:25]

참가 물질

9

반응물 5

HCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 86585896Sodium bicarbonate water

생성물 1

HCID 67067180tert-butyl N'-{5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}pentanoyl}hydrazinecarboxylate수율 92%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

HOBT (108 mg) and EDC (153 mg) were sequentially added to a solution of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid trifluoroacetic acid salt (300 mg), tert-butyl carbazate (71 mg) and IPEA (0.38 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for three hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 222 mg of the title compound. The property value of the compound is as follows.

후처리

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

출처 및 근거

ORD 기록
ord-83fe7be71a6b4320a837c604d04aaa6d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973033B2

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