tert-Butanol → HCID 131717459, compound

HRID 847050Notes

Reaction equation

HRID 847050 reaction equation
C([Li])CCC.CCCCCC.C(O)(C)(C)C.C(OC(C1C=CC=CC=1C1C=CC(C[N:37]2[C:41]([CH2:42][OH:43])=[C:40]([I:44])[N:39]=[C:38]2[CH2:45][CH2:46][CH2:47][CH3:48])=CC=1)=O)(C)(C)C.[CH3:49][O:50][CH2:51][CH2:52][O:53][CH2:54]Cl>O1CCCC1.C(OCC)C>[CH2:45]([C:38]1[NH:37][C:41]([CH2:42][O:43][CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])=[C:40]([I:44])[N:39]=1)[CH2:46][CH2:47][CH3:48]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 15698083HCID 15698083, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 131717459HCID 131717459, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.56 mL of 1.6M n-butyl-lithium/hexane in 80 mL of tetrahydrofuran at 0° was added dropwise 1.15 mL of t-butanol. To the solution was added 3.28 g of 1-[(2'-tert-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-hydroxymethyl-4-iodoimidazole followed by 1.15 mL of 2-methoxyethoxymethyl chloride. The resulting solution was stirred at 25° for 16 hours. The mixture was diluted with diethyl ether, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography afforded 2.61 g of 1-[2'-tert-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-iodo-5-(2-methoxyethoxymethoxymethyl)imidazole. NMR (200 MHz, CDCl3):δ7.78 (d, 1H); 7.43 (m, 2H); 7.28 (m, 3H); 6.98 (d, 2H); 5.26 (s, 2H); 4.69 (s, 2H); 4.45 (s, 2H); 3.68 (m, 2H); 3.57 (m, 2H); 3.37 (s, 3H); 2.58 (t, 2H); 1.67 (quint., 2H); 1.34 (sext., 2H); 1.26 (s, 9H); 0.87 (t, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16e27232fa164514b4f179d6ffd06bc9
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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