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Tetrahydrofuran → 2-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

HRID 275849
ノート
印刷プレビュー

反応式

HRID 275849 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][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=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:32]1[CH:31]=[CH:30][C:29]([CH2:28][NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[CH:34][CH:33]=1)=[O:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamateHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

生成物 1

HCID 183153642-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone収率 25%

試薬・触媒・溶媒 3

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

実験手順

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (3.21 g) and N-tert-butoxycarbonyl-4-bromobenzylamine (2.86 g) was cooled to −78° C. To the solution kas gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (31 ml). To the mixture were then added water (100 ml) and acetic acid ethyl ester (100 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography. followed by crystallization. The crystals were collected to give 2-amino-4′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (0.9 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 then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography
  5. customfollowed by crystallization
  6. customThe crystals were collected

出典と根拠

ORDレコード
ord-79d384d4b9734a568bbbe4fa09c91c97
出典データセット
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06352982B1

反応ノート

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