Imidazole → HCID 23525647、化合物

HRID 644952

反応式

HRID 644952 の反応式
[N:1](C(OCC)=O)=[N:2]C(OCC)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH:25]=2)=[C:16]([C@H:33](O)[CH3:34])[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:55]1C=CN=C1>ClCCl.[Zn](N=[N+]=[N-])N=[N+]=[N-]>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH:25]=2)=[C:16]([C@@H:33]([N:55]=[N+:1]=[N-:2])[CH3:34])[CH:15]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68519018Tert-Butyl 4-{4-Chloro-2-[(1R)-1-Hydroxyethyl]Phenyl}-3,6-Dihydropyridine-1(2H)-Carboxylate

生成物 1

HCID 23525647HCID 23525647、化合物

試薬・触媒・溶媒 2

HCID 178514646Zinc azide触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of diethyl azodicarboxylate (49.6 mL, 0.315 mol) was added dropwise to a stirred mixture of tert-butyl 4-{4-chloro-2-[(1R)-1-hydroxyethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate (26.7 g, 78.9 mmol), Zn(N3)2.2Py (prepared according to: Viaud, M-C; Rollin, P. Synthesis 1990:130-131) (48.5 g, 0.158 mol), triphenylphosphine (82.7 g, 0.315 mol) and imidazole (21.5 g, 0.315 mol) in dichloromethane at approximately 0° C. After the addition, the resulting mixture was allowed to warm to ambient temperature and stirred vigorously for 3 days. The reaction mixture was filtered through a short column of silica gel eluted with the appropriate volume of dichloromethane to remove excess salts and polar byproducts. The filtrate was concentrated in vacuo and the crude residue was purified by flash chromatography on silica gel (12.5% ethyl acetate/hexanes as eluent) to furnish the title compound as a viscous pale yellow oil.

後処理

  1. additionAfter the addition
  2. filtrationThe reaction mixture was filtered through a short column of silica gel
  3. washeluted with the appropriate volume of dichloromethane
  4. customto remove excess salts and polar byproducts
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude residue was purified by flash chromatography on silica gel (12.5% ethyl acetate/hexanes as eluent)

出典と根拠

ORDレコード
ord-9817cd2b1e83400ea35ce1dd8e1b184e
出典データセット
uspto-grants-2010_04
特許番号
US07700778B2

関連ノート

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