Dichloromethane → HCID 21196095, 화합물

HRID 1066817노트

반응식

HRID 1066817 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][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][C:10]([CH3:15])([CH3:14])[CH2:11][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 135532954-Bromo-2-(bromomethyl)-1-fluorobenzeneHCID 21196111Carbamic acid, (4-hydroxy-2,2-dimethylbutyl)-, 1,1-dimethylethyl esterHCID 23665647Potassium tert-butoxide

생성물 1

HCID 21196095HCID 21196095, 화합물수율 74.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-45 °C

실험 절차

A stirred solution of 4-(t-butoxycarbonylamino)-3,3-dimethylbutan-1-ol (1.0 g, 4.60 mmol) in tetrahydrofuran (33 ml) at −45° C. was treated with potassium t-butoxide (1 M in tetrahydrofuran, 5.06 ml, 5.06 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 (1.23 g, 4.60 mmol). The resulting yellow mixture was slowly warmed to 0° C. and stirred for about four hours. The cloudy reaction mixture was diluted wtih methylene chloride (100 ml) 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 1.38 grams (74%) of the title intermediate as a colorless oil.

후처리

  1. temperaturecooled to −78° C.
  2. temperatureThe resulting yellow mixture was slowly warmed to 0° C.
  3. stirringstirred for about four 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-263070a68c5046078afcb7451df50e5a
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06245761B1

반응 노트

불러오는 중…