(+)-Glyceraldehyde → HCID 23515257、化合物

HRID 1835175

反応式

HRID 1835175 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.[O:37]=[CH:38][C@@H:39]([CH2:41]O)[OH:40]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][N:26]([CH:41]([C:30]3[O:29][CH:33]=[CH:32][CH:31]=3)[C@H:39]([OH:40])[CH2:38][OH:37])[CH2:27][CH2:28]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

6

反応物 3

HCID 79014(+)-GlyceraldehydeHCID 2734357Furan-2-boronic acidHCID 11396034HCID 11396034、化合物

生成物 1

HCID 23515257HCID 23515257、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

2.08 g N-[(2S)-2-(3,4-dichlorophenyl)-4-(piperazinyl)butyl]-N-methylbenzamide (preparation see above under 1C) was dissolved in 100 ml ethanol and heated to approx. 50° C. 740 mg 2-furanboronic acid and 550 mg of an 80%-strength solution of D-glyceraldehyde in water were added to this initial solution. The resulting solution was heated to boiling at reflux for 10 hours. Then excess solvent was evaporated in a vacuum. Purification of the residue by column chromatography on silica gel (mobile solvent: dichloromethane/EtOH/NH4OH 87/11/2) yielded 2.1 g of the title compound as a beige foam, optical rotation [α]D20=−6.1° (c=1 in methanol); 1H-NMR (CDCl3, RT): 3.65 (d, 1H); 4.23 (ddd, 1H); 3.72 (dd, 1H); 3.78 (dd, 1H); 6.27 (d, 1H); 6.37 (1H); 7.42 (1H).

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 10 hours
  3. customThen excess solvent was evaporated in a vacuum
  4. customPurification of the residue by column chromatography on silica gel (mobile solvent: dichloromethane/EtOH/NH4OH 87/11/2)

出典と根拠

ORDレコード
ord-9506eec7136b48918ec35c609393b609
出典データセット
uspto-grants-2004_08
特許番号
US06770649B2

関連ノート

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