1-Bromooctadecane → HCID 16754950, compound

HRID 1692193Notes

Reaction equation

HRID 1692193 reaction equation
[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]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 2723671Tetrabutylammonium HydroxideHCID 16110080HCID 16110080, compound

Product 1

HCID 16754950HCID 16754950, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6d89eb9f14a0412892e72f59e5bac8bf
Source dataset
uspto-grants-2012_04
Patent number
US08153787B2

Reaction notes

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