Sodium hydride → N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine

HRID 1734687ノート

反応式

HRID 1734687 の反応式
[C:1]([NH:20][CH:21]([CH2:24][OH:25])[CH2:22][OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Br)=[CH:39][CH:38]=1>C1COCC1.C(Cl)Cl>[C:1]([NH:20][CH:21]([CH2:22][OH:23])[CH2:24][O:25][CH2:41][C:40]1[CH:43]=[CH:44][C:37]([C:29]2[O:28][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=2)=[CH:38][CH:39]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 18427762N-trityl-1,3-dihydroxy-2-propanamine

生成物 1

HCID 19420787N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

N-trityl-1,3-dihydroxy-2-propanamine (3.7 g; 11 mmol) is dissolved in THF (22 ml) and cooled to 0° C. NaH (0.44 g; 11 mmol; 60% in oil) is added and the reaction is warmed to room temperature and allowed to stir for 2 hours. 4-(benzoxazol-2-yl)benzylbromide (1.6 g; 5.5 mmol) is added and the reaction allowed to stir for 15 hours. The reaction is diluted with CH2Cl2 and washed with H2O 2x, dried (Na2SO4), concentrated and purified by column chromatography with basic alumina and eluted with 2% MeOH/98% CH2Cl2 to obtain N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine as a white solid which is used directly in Step E.

後処理

  1. temperaturethe reaction is warmed to room temperature
  2. stirringto stir for 15 hours
  3. washwashed with H2O 2x
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography with basic alumina
  7. washeluted with 2% MeOH/98% CH2Cl2

出典と根拠

ORDレコード
ord-a25c44df0ab64d979eb786525a5f8468
出典データセット
uspto-grants-1996_07
特許番号
US05534532

反応ノート

読み込み中…