1-Bromooctadecane → HCID 16754950、化合物

HRID 1692193ノート

反応式

HRID 1692193 の反応式
[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.O[CH2:20][C@@H:21]([O:31][CH2:32][P:33]([OH:36])([OH:35])=[O:34])[CH2:22][N:23]1[CH:30]=[N:29][C:27]([NH2:28])=[N:26][C:24]1=[O:25].[CH2:37](Br)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>CO>[CH3:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][O:36][P:33]1([O:34][CH2:20][C@H:21]([CH2:22][N:23]2[C:24](=[O:25])[N:26]=[C:27]([NH2:28])[N:29]=[CH:30]2)[O:31][CH2:32]1)=[O:35]

参加物

5

反応物 3

HCID 82181-BromooctadecaneHCID 2723671Tetrabutylammonium HydroxideHCID 16110080HCID 16110080、化合物

生成物 1

HCID 16754950HCID 16754950、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

1 M Methanolic tetrabutylammonium hydroxide (0.61 ml; 0.61 mmol) was added to a solution of cyclic HPMP-5-azaC (161 mg, 0.61 mmol) in absolute methanol (50 ml), the mixture stirred for 5 min, then evaporated and the residue coevaporated with toluene (20 ml), followed by dry dioxane (20 ml). The residue was dissolved in dioxane (10 ml) and stirred with octadecyl bromide (500 mg, 1.5 mmol) at 95° C. for 3 h. The reaction mixture was evaporated, the residue chromatographed on a column of silica gel (30 ml) in system chloroform-methanol (85:15). Yield: 250 mg, 80%, white solid. ESI MS: 1051.0 (2M+Na)+ (41), 537.3 (M+Na)+ (64), 515.3 (23) (MH)+. HRMS (ESI): For C25H48N4O5P (MH+) calculated: 515.3362. Found: 515.3382. 1H NMR (DMSO-d6): 8.11 s, 1H (H-6); 7.46 brs, 1H and 7.45 brs, 1H (NH2); other signals not distinguished. 13C NMR (DMSO-d6): 166.50 (C-4); 159.62 (C-6); 153.95 (C-2); 73.19 d, J (P, C)=4.9 (C-2′); 72.04 d, J (P, C)=12.4 (C-3′); 65.19 d, J (P, C)=5.9 (OCH2); 62.70 d, J (P, C)=141.6 (P—C); 45.75 (C-1′); 31.44, 30.03, 29.18, 5 C, 29.09, 25.09, 23.24, 5 C, 22.24 and 19.37 (CH2); 13.65 (CH3).

後処理

  1. customevaporated
  2. dissolutionThe residue was dissolved in dioxane (10 ml)
  3. customThe reaction mixture was evaporated
  4. customthe residue chromatographed on a column of silica gel (30 ml) in system chloroform-methanol (85:15)
  5. custom72.04 d, J (P, C)=12.4
  6. custom65.19 d, J (P, C)=5.9 (OCH2)
  7. custom62.70 d, J (P, C)=141.6 (P—C)

出典と根拠

ORDレコード
ord-6d89eb9f14a0412892e72f59e5bac8bf
出典データセット
uspto-grants-2012_04
特許番号
US08153787B2

反応ノート

読み込み中…