Triethylamine → HCID 178484575, 화합물

HRID 630402노트

반응식

HRID 630402 반응식
[OH:1][C:2]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][CH3:13])[CH2:8][CH2:7]1)=[O:4].Br[CH2:25][CH2:26][OH:27].C(N(CC)CC)C.BrC(O)C>C(#N)C.C1COCC1>[OH:1][C:2]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:25][CH2:26][OH:27])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

참가 물질

7

반응물 4

HCID 8471Triethylamine2회HCID 108982-BromoethanolHCID 14202443Ethanol, 1-bromo-HCID 178484861HCID 178484861, 화합물2회

생성물 1

HCID 178484575HCID 178484575, 화합물수율 76%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
80 °C

실험 절차

A mixture of trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5; 300 mg; 0.85 mmol), 2-bromoethanol (0.145 ml; 2.05 mmol) and triethylamine (0.36 ml; 2.58 mmol) in 4.5 ml of acetonitrile and 3.5 ml of THF was stirred at 80° C. in a sealed vessel for 16 hr. Additional amounts of bromoethanol (0.145 ml; 2.05 mmol), triethylamine (0.36 ml; 2.58 mmol), acetonitrile (3.5 ml) and THF (3.5 ml) were added and the stirring and heating prosecuted for 24 additional hours. The solution was evaporated to dryness, dissolved in dichloromethane, washed with brine, dried and concentrated. Purification by preparative reversed-phase HPLC (Cl3CH/MeOH from 1:0 to 9:1) gave 76% of the title product as a colourless oil.

후처리

  1. temperaturethe stirring and heating
  2. customThe solution was evaporated to dryness
  3. dissolutiondissolved in dichloromethane
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customPurification by preparative reversed-phase HPLC (Cl3CH/MeOH from 1:0 to 9:1)

출처 및 근거

ORD 기록
ord-45f3946e87604b64b18545a6efa41cf4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315463B2

반응 노트

불러오는 중…