Dichloromethane → HCID 21195983、化合物

HRID 1066816ノート

反応式

HRID 1066816 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[F:22][C:23]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:24]=1[CH2:25]Br.C(Cl)Cl>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][O:13][CH2:25][C:24]1[CH:27]=[C:28]([Br:31])[CH:29]=[CH:30][C:23]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 109659694-(t-butoxycarbonylamino)-2,2-dimethylbutanolHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 21195983HCID 21195983、化合物収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-45 °C

実験手順

A stirred solution of 4-(t-butoxycarbonylamino)-2,2-dimethylbutan-1-ol (1.5 g, 6.90 mmol) in tetrahydrofuran (49 ml) at −45° C. was treated with potassium t-butoxide (1 M in tetrahydrofuran, 7.59 ml, 7.59 mmol). The anion was stirred for 30 minutes at −45° C., then cooled to −78° C. and treated with a tetrahydrofuran solution of 2-fluoro-5-bromobenzyl bromide (1.85 g, 6.90 mmol). The resulting yellow mixture was slowly warmed to ambient temperature and stirred for about 18 hours. The cloudy reaction mixture was diluted wtih methylene chloride and washed with 1 M potassium carbonate. The organic fraction was dried over sodium sulfate, filtered, and the solvents were removed in vacuo. The residue was further purified by preparative high performance liquid chromatography to yield 1.45 grams (52%) of the title intermediate as a colorless oil.

後処理

  1. temperaturecooled to −78° C.
  2. temperatureThe resulting yellow mixture was slowly warmed to ambient temperature
  3. stirringstirred for about 18 hours
  4. customThe cloudy reaction mixture
  5. washwashed with 1 M potassium carbonate
  6. dry with materialThe organic fraction was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents were removed in vacuo
  9. customThe residue was further purified by preparative high performance liquid chromatography

出典と根拠

ORDレコード
ord-c9eb6c5f4d7243abafdf9287c56bcb47
出典データセット
uspto-grants-2001_06
特許番号
US06245761B1

反応ノート

読み込み中…