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 599558ノート

反応式

HRID 599558 の反応式
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]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6b62e2ffcd754f49aa716544549b0e6a
出典データセット
uspto-grants-2011_03
特許番号
US07897632B2

反応ノート

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