Triethylamine → HCID 178484575、化合物

HRID 630402ノート

反応式

HRID 630402 の反応式
[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]

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 108982-BromoethanolHCID 14202443Ethanol, 1-bromo-HCID 178484861HCID 178484861、化合物2 回

生成物 1

HCID 178484575HCID 178484575、化合物収率 76%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-45f3946e87604b64b18545a6efa41cf4
出典データセット
uspto-grants-2016_04
特許番号
US09315463B2

反応ノート

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