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

HRID 275852ノート

反応式

HRID 275852 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9760d44486f5462d9b746c158417ff9c
出典データセット
uspto-grants-2002_03
特許番号
US06352982B1

反応ノート

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