Ethyl Acetate → Ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 52905Notes

Reaction equation

HRID 52905 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C:14]1[N:15]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[N:46]([C:47]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:45]=[N:44][N:43]=3)=[CH:32][CH:31]=2)[C:16]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:17]([C:19](OCC)=[O:20])[N:18]=1)[CH2:12][CH3:13].C(OCC)(=O)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[OH:20][CH2:19][C:17]1[N:18]=[C:14]([CH2:11][CH2:12][CH3:13])[N:15]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[N:46]([C:47]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[N:45]=[N:44][N:43]=3)=[CH:34][CH:35]=2)[C:16]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19036089Diethyl 2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-4,5-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19036205Ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 ml of a 1.5M solution of diisobutylaluminum hydride in toluene were added dropwise at -20° C. under an atmosphere of nitrogen to a solution of 4.27 g of diethyl 2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-4,5-dicarboxylate [prepared as described in step (a) above] in 50 ml of tetrahydrofuran. The resulting mixture was allowed to stand at 0° C. for 16 hours and then mixed with ethyl acetate and with a saturated aqueous solution of ammonium chloride; it was then stirred at room temperature for 1 hour. The resulting precipitate was filtered off, and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate; the solvent was then removed by distillation under reduced pressure. The crystalline residue was washed with diisopropyl ether, to give 4.03 g of the title compound, melting at 135°-138° C.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customthe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation under reduced pressure
  5. washThe crystalline residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-e6c83024f5214e589b1522b143eefd1b
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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