Methanol → HCID 44201124, 화합물

HRID 1486472노트

반응식

HRID 1486472 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 44201124HCID 44201124, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-58c7b81487564db6ab101db74a1ebf5c
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428448B2

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