Acetic Acid → HCID 178441672, compound

HRID 1735832Notes

Reaction equation

HRID 1735832 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[N:40](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:39]=[N:38][N:37]=3)=[CH:26][CH:25]=2)[C:7]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([OH:22])=[O:21])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(O)(=O)C.O>C1COCC1>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[NH:40][N:39]=[N:38][N:37]=3)=[CH:26][CH:25]=2)[C:7]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([OH:22])=[O:21])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 19434486HCID 19434486, compound

Product 1

HCID 178441672HCID 178441672, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 450 mg of 2-butyl-5-[(2-carboxyphenyl)methoxymethyl]-4-chloro-1-[[2'-(1-triphenylmethyltetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]-1H-imidazole, 7.5 ml of acetic acid, 3.7 ml of H2O and 2 ml of THF is stirred at room temperature for 10 hours. The solvent s are evaporated off under reduced pressure and the residue is taken up in H2O, alkalinized with 10% NaOH, an insoluble part is filtered off, the resulting solution is extracted with ether and acidified to pH 4.5 with 5N HCl. The obtained precipitate is filtered and washed with H2O. 0.2 g of a white solid are obtained (70% yield). M.p. 109°-111° C. 1H NMR (CDCl3), δ: 0.84 (t, 3 H); 1.27 (m, 2 H); 1.54 (m, 2 H); 2.39 (t, 2 H); 4.43 (s, 2 H); 4.60 (s, 2 H); 5.14 (s, 2 H); 6.80-8.12 (m, 12 H).

Workup

  1. customThe solvent s are evaporated off under reduced pressure
  2. filtrationan insoluble part is filtered off
  3. extractionthe resulting solution is extracted with ether
  4. filtrationThe obtained precipitate is filtered
  5. washwashed with H2O

Sources & evidence

ORD record
ord-74815852b90a4aab9020e2557691833f
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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