Hexane → 2-Amino-3'-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone

HRID 275867ノート

反応式

HRID 275867 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(OC)[C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[NH2:28].CCCCCC.C([Li])CCC>O1CCCC1.C(OCC)(=O)C.O>[NH2:28][C:22]1[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=1[C:20]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=1)=[O:29]

参加物

8

反応物 4

HCID 8058HexaneHCID 18315328Tert-butyl 3-bromophenethylcarbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 183153892-Amino-3'-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone収率 70.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-tert-butoxycarbonyl-3-bromophenethylamine (1.7 g) and N-methyl-N-methyloxy-2-amino-5-chloro-benzamide (1.9 g) in tetrahydrofuran (50 ml) was cooled to -70° C. To the solution was added dropwise, while stirring, a hexane solution of n-butyl lithium (1.6 mol/L) (18 ml). To the reaction mixture were added water (100 ml) and ethyl acetate (80 ml). The mixture was shaken. The organic layer was separated, which was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-amino-3′-(2-tert-butoxycarbonylaminoethyl)-5-chloro-benzophenone (1.5 g) as a yellow crystalline product. m.p.: 128-129° C.

後処理

  1. additionTo the solution was added dropwise
  2. stirringThe mixture was shaken
  3. customThe organic layer was separated
  4. washwhich was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica gel column chromatography

出典と根拠

ORDレコード
ord-52e078ed5ef54f3082b3b1bda7d562bb
出典データセット
uspto-grants-2002_03
特許番号
US06352982B1

反応ノート

読み込み中…