Triethylamine → 1-[[[(4-isothiocyanatophenyl)carbonyl]amino]butyl]-N,N-diethyl-D-lysergamide

HRID 1108001

反応式

HRID 1108001 の反応式
NC(C)[CH2:3][CH2:4][N:5]1[C:26]2[C:27]3[C:7]([CH2:8][C@@H:9]4[C:21]([C:22]=3[CH:23]=[CH:24][CH:25]=2)=[CH:20][C@@H:12]([C:13](=[O:19])[N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:11][N:10]4[CH3:28])=[CH:6]1.[N:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)=[C:31]=[S:32].[CH2:42]([N:44](CC)CC)[CH3:43]>C1COCC1>[N:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:44][CH2:42][CH2:43][CH2:3][CH2:4][N:5]2[C:26]3[C:27]4[C:7]([CH2:8][C@@H:9]5[C:21]([C:22]=4[CH:23]=[CH:24][CH:25]=3)=[CH:20][C@@H:12]([C:13](=[O:19])[N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:11][N:10]5[CH3:28])=[CH:6]2)=[O:38])=[CH:35][CH:34]=1)=[C:31]=[S:32]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 6376544-Isothiocyanatobenzoyl chlorideHCID 228945521-(3-aminobutyl)-N,N-diethyl-D-lysergamide

生成物 1

HCID 228945541-[[[(4-isothiocyanatophenyl)carbonyl]amino]butyl]-N,N-diethyl-D-lysergamide収率 62.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 370 mg (0.94 mmol) of 5 in 15 mL of dry THF was cooled to 0° C. and treated with a solution of 190 mg (0.96 mmol) of 6 in 5 mL of dry THF, stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was treated with 0.14 mL (1.0 mmol) of triethylamine and stirred at room temperature for 2 hours The reaction mixture was concentrated at reduced pressure. The residue was dissolved in methylene chloride, washed with H2O, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was chromatographed on 200 g of silica gel using 3% methanol in methylene chloride as eluent to yield 325 mg (62%) of 7 as a tan amorphous solid [α]D =+47.5° (c=0.91%; CHCl3).

後処理

  1. customat room temperature
  2. customovernight
  3. stirringstirred at room temperature for 2 hours The reaction mixture
  4. concentrationwas concentrated at reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with H2O
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on 200 g of silica gel using 3% methanol in methylene chloride as eluent

出典と根拠

ORDレコード
ord-8a45b5c874d444979f4cb3e09adc6b78
出典データセット
uspto-grants-2000_05
特許番号
US06063908

関連ノート

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