Ethyl Acetate → HCID 18962493, compound

HRID 1707764Notes

Reaction equation

HRID 1707764 reaction equation
O[CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]([CH2:45][CH2:46][CH3:47])=[N:5][C:4]=1C=O.C([O:53][CH2:54][CH3:55])(=O)C>C1COCC1>[OH:53][CH2:54][C:55]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25]([C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:24]=[N:23][N:22]=3)=[CH:13][CH:14]=2)[C:6]([CH2:45][CH2:46][CH3:47])=[N:5][C:4]=1[CH:3]=[CH2:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 18962499HCID 18962499, compound

Product 1

HCID 18962493HCID 18962493, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The suspension became a dark yellow solution. Afterwards, a solution of 5-hydroxymethyl-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole-4-carboxaldehyde (1.31 g, 2.0 mmol, 1.0 eq) in THF (minimum to dissolve) was added thereto and the resultant light milky yellow solution was stirred overnight at room temperature. The solution was diluted with ethyl acetate and washed with water (3×). The organic layer was dried (MgSO4), the solvent removed in vacuo, and the residue flash chromatographed over silica gel in 1:1 hexane/ethyl acetate to yield 620 mg (48%) of a white glass: NMR (DMSO-d6) δ 7.79 (d,1H,J=7Hz); 7.62 (t,1H,J=7Hz); 7.55 (t,1H,J=7Hz); 7.45 (d,1H,J=7Hz); 7.41-7.18 (m,9H); 7.06 (d,2H,J=9Hz); 6.95-6.80 (m,8H); 6.80-6.55 (m,1H); 5.73 (d of d,1H,J=17,3 Hz); 5.17 (s,2H); 5.10 (t,1H,J=7Hz); 5.05 (d of d,1H,J=12,3Hz); 4.28 (d,2H,J=7Hz); 2.37 (t,2H,J=7Hz); 1.50 (t of q,2H,J=7,7Hz); 0.78 (t,3H,J=7Hz). IR (neat) 1029; 1006; 909; 733; 698 cm-1. Anal. calcd. for C42H38N6O.H2O: C, 76.34; H, 6.10; N, 12.72. Found: C, 76.49; H, 5.88; N, 12.52. ##STR80##

Workup

  1. washwashed with water (3×)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customthe residue flash chromatographed over silica gel in 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-f12aee8e6be641608dbadb7aea09d590
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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