Water → HCID 178437624, compound

HRID 1707766Notes

Reaction equation

HRID 1707766 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:6]([CH:11]=[O:12])=[C:7]([CH:9]=[CH2:10])[N:8]=1)[CH2:2][CH3:3].FC(F)(F)C(O)=O.O.[OH-].[Na+]>C1COCC1>[CH2:1]([C:4]1[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:6]([CH:11]=[O:12])=[C:7]([CH:9]=[CH2:10])[N:8]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 18962496HCID 18962496, compound

Product 1

HCID 178437624HCID 178437624, compoundYield 131.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-4-vinyl-imidazole-5-carboxaldehyde (330 mg), trifluoroacetic acid (1.65 mL), water (1.65 mL), and THF (1.65 mL) were mixed and stirred at room temperature. After 8 h, the mixture was neutralized to pH=7 with 10N NaOH and the solvents removed in vacuo. The residue was flash chromatographed in 1:1 hexane/ethyl acetate to 100% ethanol to yield 270 mg of a white glass. NMR (DMSO-d6) δ 9.92 (s,1H); 7.65-7.50 (m,1H); 7.50-7.12 (m,3H); 7.09 (d,2H,J=9Hz); 6.89 (d,2H,J=9Hz); 6.11 (d of d1H,J=17,3Hz); 5.55 (s,2H); 5.45 (d of d, 1H,J=12,3 Hz); 2.63 (t,2H,J=7Hz); 1.64 (t of q,2H,J=7,7Hz); 0.90 (t,3H,J= 7Hz). IR (Nujol) 1680 cm-1.

Workup

  1. customthe solvents removed in vacuo
  2. customchromatographed in 1:1 hexane/ethyl acetate to 100% ethanol

Sources & evidence

ORD record
ord-e001e40e3cac43ffba15825d8a644d98
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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