Acetic Acid → tert-Butyl [3-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)phenyl]carbamate

HRID 541896ノート

反応式

HRID 541896 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[C:18]#[C:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[CH:24][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.C(O)(=O)C>[Fe].O>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([C:18]#[C:19][C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[CH:24][CH:25]=2)[CH:11]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 887MethanolHCID 57962078tert-Butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate

生成物 1

HCID 57962363tert-Butyl [3-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)phenyl]carbamate収率 91%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Into the reaction flask was added tert-butyl [3-({2-[(tert-butoxycarbonyl)amino]-5-nitrophenyl}ethynyl)phenyl]carbamate (2.7 g, 6.0 mmol), methanol (70 mL), acetic acid (10 mL), and water (7 mL). Then iron powder (1.8 g, 30 mmol) was added. The reaction mixture was heated at 60° C. for 3 h. After filtration, the cake was rinsed with EtOAc. The filtrate was concentrated and the residue was diluted with NaHCO3 (aq) and EtOAc. After the layers were separated, the organic layer was dried, filtered and concentrated to give the desired product (2.3 g, 91%). LCMS for C24H30N3O4 (M+H)+: m/z=424.2.

後処理

  1. filtrationAfter filtration
  2. washthe cake was rinsed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. additionthe residue was diluted with NaHCO3 (aq) and EtOAc
  5. customAfter the layers were separated
  6. customthe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f6c9b5dca0de4f5bbb380091433aebc6
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

反応ノート

読み込み中…