Methanol → HCID 44201124、化合物

HRID 1486472ノート

反応式

HRID 1486472 の反応式
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.CO.[NH2:38][C@H:39]([CH2:43][OH:44])[CH:40]([CH3:42])[CH3:41]>N1C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH:38][C@H:39]([CH2:43][OH:44])[CH:40]([CH3:42])[CH3:41])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

7

反応物 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 445639Oleic AcidHCID 640993L-Valinol

生成物 1

HCID 44201124HCID 44201124、化合物

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a round bottom flask, oleic acid (1) (1.53 g, 5.33 mmol) was dissolved in 20 ml of dry pyridine (over KOH). To the solution TEA (0.74 ml, 5.33 mmol), DCC (1.1 g, 5.33 mmol), and NHS (0.55 g, 4.85 mmol) were added. The mixture was stirred at room temperature for overnight. After confirming the total conversion of the acid to the NHS intermediate using TLC (5% MeOH), L-Valinol (0.5 g, 4.85 mmol) was added and the mixture was stirred for additional 24 hours. After completion of the reaction (TLC: 100% Ethyl acetate), volatiles were removed under reduced pressure to dryness. The gum was dissolved in 5 ml DCM and the desired product oleoyl-valinol (10) was obtained using column chromatography (dichloromethane/ethyl acetate=1:1, v/v)). Colorless viscous oil (0.94 g, 46.8 yield).

後処理

  1. additionwas added
  2. stirringthe mixture was stirred for additional 24 hours
  3. customwere removed under reduced pressure to dryness
  4. dissolutionThe gum was dissolved in 5 ml DCM

出典と根拠

ORDレコード
ord-58c7b81487564db6ab101db74a1ebf5c
出典データセット
uspto-grants-2016_08
特許番号
US09428448B2

反応ノート

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