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

HRID 275867노트

반응식

HRID 275867 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52e078ed5ef54f3082b3b1bda7d562bb
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352982B1

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