Dichloromethane → HCID 21195983, 화합물

HRID 1066816노트

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HRID 1066816 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 21195983HCID 21195983, 화합물수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-45 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c9eb6c5f4d7243abafdf9287c56bcb47
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06245761B1

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