Acetic Acid → {4-[2-Amino-4-(5-bromo-pyridin-2-ylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 605060ノート

反応式

HRID 605060 の反応式
[C:1](O)(=O)[CH3:2].[CH2:5](O)[CH3:6].Cl[C:9](Cl)(Cl)[CH2:10][O:11][C:12](=[O:40])[NH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:36])[NH:28][C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][N:30]=3)=[CH:23][C:22]=2[N+:37]([O-])=O)=[CH:16][CH:15]=1>CCOC(C)=O.O.[Fe]>[CH:2]1[C:1]2[CH:9]([CH2:10][O:11][C:12](=[O:40])[NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20][C:21]4[CH:26]=[CH:25][C:24]([C:27](=[O:36])[NH:28][C:29]5[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][N:30]=5)=[CH:23][C:22]=4[NH2:37])=[CH:16][CH:15]=3)[C:5]3[C:6](=[CH:26][CH:21]=[CH:22][CH:23]=3)[C:16]=2[CH:15]=[CH:14][CH:19]=1

参加物

7

反応物 3

HCID 176Acetic AcidHCID 702EthanolHCID 67040335{4-[4-(5-Bromo-pyridin-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

生成物 1

HCID 67040714{4-[2-Amino-4-(5-bromo-pyridin-2-ylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester収率 97%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 5 liter, 3-neck round bottom flask equipped with a water condenser, heating mantle and overhead stirrer was charged with glacial acetic acid (0.75 L) and 200 proof ethanol (0.75 L) followed by addition of the product from Example 17C (40.0 g, 60 mmol) and iron powder (13.3 g, 240 mmol). The mixture was then heated to reflux for 6 hours, cooled to ambient temperature and diluted with 1.0-1.5 L of EtOAc, stirred for 10-15 minutes and diluted with 1.0 L of water. The two-phase mix was stirred vigorously for 5-10 minutes and the layers were allowed to separate. The red aqueous layer was removed and discarded. The remaining EtOAc layer with suspended solids was washed 6×1.0 L with water eventually removing all of the red color. The EtOAc layer was then filtered to collect a cream colored solid which was rinsed with 300 mL EtOAc and dried to constant mass in a vacuum oven (40° C., house vacuum, 24 hours) to give of the title compound (37 g, 97%).

後処理

  1. customA 5 liter, 3-neck round bottom flask equipped with a water condenser
  2. temperatureheating mantle and overhead stirrer
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 6 hours
  5. additionThe two-phase mix
  6. stirringwas stirred vigorously for 5-10 minutes
  7. customto separate
  8. customThe red aqueous layer was removed
  9. washwas washed 6×1.0 L with water
  10. customeventually removing all of the red color
  11. filtrationThe EtOAc layer was then filtered
  12. customto collect a cream colored solid which
  13. washwas rinsed with 300 mL EtOAc
  14. customdried to constant mass in a vacuum oven (40° C., house vacuum, 24 hours)

出典と根拠

ORDレコード
ord-9365b98b44344ed492bcee70832bd497
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

読み込み中…