Tetrahydrofuran → 2-Amino-4'-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone

HRID 275852노트

반응식

HRID 275852 반응식
O1CCCC1.CN(OC)[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16].[C:20]([O:24][C:25]([NH:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](Br)[CH:31]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:35][CH:34]=1)=[O:17]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 18315328Tert-butyl 3-bromophenethylcarbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

생성물 1

HCID 183153782-Amino-4'-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone수율 53%

시약·촉매·용매 3

HCID 962Water용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

A tetrahydrofuran (70 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (6.4 g) and N-tert-butoxycarbonyl-3-bromophenethylamine (6.0 g) was cooled to −78° C., to which was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (67 ml). To the mixture were then added water (300 ml) and acetic acid ethyl ester (300 ml). The organic layer was washed with water and dried over anhydrous MgSO4, and the solvent was distilled off. The residual oily compound was purified by means of a silica gel column chromatography, followed by recrystallization from hexane to afford 2-amino-4′-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone (3.97 g) as a pale yellow crystalline product.

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationthe solvent was distilled off
  4. customThe residual oily compound was purified by means of a silica gel column chromatography
  5. customfollowed by recrystallization from hexane

출처 및 근거

ORD 기록
ord-9760d44486f5462d9b746c158417ff9c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352982B1

반응 노트

불러오는 중…