1,10-Phenanthroline → HCID 21071235、化合物

HRID 1372172ノート

反応式

HRID 1372172 の反応式
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])C1C=CC=CC=1.I[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[C:32]([O-:35])([O-])=[O:33].[K+].[K+].N1[C:51]2[C:42](=[CH:43][CH:44]=[C:45]3[C:50]=2N=CC=C3)[CH:41]=CC=1>CS(C)=O.[Cu]I.O.CCOC(C)=O>[CH2:41]([O:35][C:32]([C:11]1([NH2:10])[CH2:16][CH2:15][CH2:14][N:13]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[C:12]1=[O:17])=[O:33])[C:42]1[CH:51]=[CH:50][CH:45]=[CH:44][CH:43]=1

参加物

9

反応物 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 13556445Benzyl (2-oxopiperidin-3-yl)carbamateHCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid

生成物 1

HCID 21071235HCID 21071235、化合物

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

Part A. To a mixture of (2-oxo-piperidin-3-yl)-carbamic acid benzyl ester (1.35 g, 5.44 mmol) and 1-(4-iodo-phenyl)-cyclopropanecarboxylic acid (1.56 g, 5.42 mmol, 1.0 eq) in DMSO (5 mL) was added K2CO3 (3.00 g, 21.73 mmol, 4.0 eq), CuI (0.52 g, 2.74 mmol, 0.5 eq), and 1,10-phenanthroline (0.50 g, 2.74 mmol, 0.5 eq) sequentially. The mixture was heated at 120° C. overnight under N2. After cooling, EtOAc and H2O was added. The mixture was filtered. The filtrate was washed with 1N NaOH. The aqueous layer was acidified with conc. HCl, and extracted with EtOAc (3×). The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give crude 1-[4-(3-benzyloxycarbonyl-amino-2-oxo-piperidin-1-yl)-phenyl]-cyclopropanecarboxylic acid (0.69 g, slightly contaminated with disubstituted compound). LC/MS (ESI) 409.2 (M+H).

後処理

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered
  3. washThe filtrate was washed with 1N NaOH
  4. extractionextracted with EtOAc (3×)
  5. washThe organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca2910d92ab944c1b0f43c78076e8121
出典データセット
uspto-grants-2007_01
特許番号
US07157470B2

反応ノート

読み込み中…