Cesium carbonate → [(R)-2-(2-nitro-phenylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester

HRID 1711192ノート

反応式

HRID 1711192 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[N+:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1I)([O-:20])=[O:19].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:10][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N+:18]([O-:20])=[O:19])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 69115o-IodonitrobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 15675183[(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER

生成物 1

HCID 68777129[(R)-2-(2-nitro-phenylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester収率 64.6%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a degassed solution of ((R)-2-amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester (400 mg, 1.69 mmol) in toluene (10 ml), was added 2-nitroiodobenzene (423 mg, 1.69 mmol), Pd2 (dba)3 (31 mg, 0.34 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (39 mg, 0.68 mmol) and Cs2CO3 (551 mg, 1.69 mmol). The mixture was heated at 110° C. for 24 h. It was then concentrated and the residue was purified using column chromatography (4:1, Hexanes/EtOAc) to give [(R)-2-(2-nitro-phenylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester (390 mg, 64%).

後処理

  1. concentrationIt was then concentrated
  2. customthe residue was purified

出典と根拠

ORDレコード
ord-450e4c7d594a41eb9ec256a97659774b
出典データセット
uspto-grants-2010_09
特許番号
US07790747B2

反応ノート

読み込み中…