Hexane → 2-Amino-3-tert-butoxycarbonylaminomethyl-4-chlorobenzophenone

HRID 275863노트

반응식

HRID 275863 반응식
CN(OC)[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11].[C:15]([O:19][C:20]([NH:22][CH2:23]C1C=CC=C(Br)C=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[CH3:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].C([Li])CCC>O1CCCC1.O>[NH2:11][C:5]1[C:6]([CH2:23][NH:22][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:3]([C:33]1[CH:32]=[CH:31][CH:36]=[CH:35][CH:34]=1)=[O:12]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 11033439tert-Butyl 3-bromobenzylcarbamateHCID 222292422-amino-4-chloro-N-methoxy-N-methylBenzamideHCID 178418339Butyllithium

생성물 1

HCID 183153472-Amino-3-tert-butoxycarbonylaminomethyl-4-chlorobenzophenone

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

N-methyl-N-methyloxy-2-amino-4-chlorobenzamide (3.6 g) and N-tert-butoxycarbonyl-3-bromobenzylamine (5.5 g) were dissolved in tetrahydrofuran (50 ml). The solution was cooled to −78° C., to which was added dropwise, while stirring, a hexane solution of n-butyl lithium (1.6 mol/L, 60 ml) over 40 minutes. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate (150 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was purified by means of a silica gel column chromatography to give 2-amino-3-tert-butoxycarbonylaminomethyl-4-chlorobenzophenone as a yellow oily product (2.3 g).

후처리

  1. additionwas added dropwise
  2. extractionwas subjected to extraction with ethyl acetate (150 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by means of a silica gel column chromatography

출처 및 근거

ORD 기록
ord-7c1e89ae5dac449c85909539cb34bc66
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352982B1

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