Benzyl Alcohol → HCID 11606270, compound

HRID 1432434Notes

Reaction equation

HRID 1432434 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]3[N:28]=[C:29]([C:39]45[CH2:46][CH2:45][C:42](C(O)=O)([CH2:43][CH2:44]4)[CH2:41][CH2:40]5)[NH:30][C:31]=3[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=3)=[CH:26][C:21]=2[O:20][CH2:19]1.C([N:53]([CH:56](C)C)CC)(C)C.[CH2:59]([OH:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C1(C)C=CC=CC=1>[CH2:59]([O:66][C:56](=[O:8])[NH:53][C:42]12[CH2:43][CH2:44][C:39]([C:29]3[NH:30][C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=4)=[C:27]([C:25]4[CH:24]=[CH:23][C:22]5[O:18][CH2:19][O:20][C:21]=5[CH:26]=4)[N:28]=3)([CH2:46][CH2:45]1)[CH2:40][CH2:41]2)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10388029HCID 10388029, compound

Product 1

HCID 11606270HCID 11606270, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diphenylphosphoryl azide (0.070 mL, 0.324 mmol) was added to a solution of 4-[4-benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl]-bicyclo[2.2.2]octane-1-carboxylic acid (see Example 22; 0.140 g, 0.324 mmol) and diisopropylethylamine (0.068 mL, 0.39 mmol) in toluene (5 mL). The mixture was stirred for 2 hours. Benzyl alcohol (0.067 mL, 0.648 mmol) was added to the mixture. The mixture was stirred at room temperature for 18 hours. Solvent was removed. The mixture was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.002 g (1%) of the title compound as a yellow solid. MS (ESP+) m/z 537.4 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.71 (m, 1H), 7.33 (m, 5H), 7.22 (m, 2H), 6.97 (m, 3H), 6.05 (s, 2H), 5.02 (s, 2H), 2.63 (s, 3H), 2.17 (m, 6H), 2.06 (m, 6H).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customSolvent was removed
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customHPLC purification
  9. washeluting with acetonitrile

Sources & evidence

ORD record
ord-b436bbf99e7249e3b8af7c7e68b22b94
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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