Lysergic Acid → (+)-Lysergic acid diethylamide

HRID 1016659

反応式

HRID 1016659 の反応式
O[C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=[O:3].[C:21](C1NC=CN=1)([C:23]1[NH:24][CH:25]=[CH:26]N=1)=O.C(NCC)C>CN(C=O)C>[CH3:21][CH2:23][N:24]([C:2]([C@@H:4]1[CH:19]=[C:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]=42)[NH:12][CH:11]=3)[N:6]([CH3:7])[CH2:5]1)=[O:3])[CH2:25][CH3:26]

参加物

5

反応物 3

HCID 6717Lysergic AcidHCID 8021DiethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

生成物 1

HCID 5761(+)-Lysergic acid diethylamide収率 75.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4.0 g (0.015 mol) of D-lysergic acid and 200 mL of dry DMF, under argon, was treated with 3.6 g (0.022 mol) of carbonyl diimidazole and stirred at room temperature for 1 hour. The reaction was treated with 15.2 mL (0.15 mol) of diethylamine and stirred at room temperature overnight. The reaction was concentrated at reduced pressure. The residue was taken up in 250 mL of CH2Cl2 and washed with 250 mL of H2O. Insoluble material was removed by filtration and the layers were separated. The organic portion was washed with 250 mL of saturated brine solution, dried over anhydrous Na2SO4 and concentrated at reduced pressure. The residue was chromatographed on 500 g of silica gel using 3% CH3OH in CH2Cl2 as eluent to yield 3.65 g (75.7%) of D-LSD [α]D=+50.4° (c=1%; CHCl3) as a light brown amorphous solid. The 8 α-epimer (also known as iso-LSD) has [α]D=+226° (c=1%; CHCl3).

後処理

  1. stirringstirred at room temperature overnight
  2. concentrationThe reaction was concentrated at reduced pressure
  3. washwashed with 250 mL of H2O
  4. customInsoluble material was removed by filtration
  5. customthe layers were separated
  6. washThe organic portion was washed with 250 mL of saturated brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on 500 g of silica gel using 3% CH3OH in CH2Cl2 as eluent

出典と根拠

ORDレコード
ord-4e08d6a8612b4a74a0ded06e0fd4a8b8
出典データセット
uspto-grants-2002_11
特許番号
US06476199B1

関連ノート

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