Tritylolmesartan medoxomil → HCID 178440075, compound

HRID 52956Notes

Reaction equation

HRID 52956 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:58][CH2:59][CH3:60])[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[N:38](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:9]=1[C:10]([O:12][CH2:13][C:14]1[O:15][C:16](=[O:20])[O:17][C:18]=1[CH3:19])=[O:11])([CH3:4])[CH3:3]>C(O)(=O)C>[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:58][CH2:59][CH3:60])[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:9]=1[C:10]([O:12][CH2:13][C:14]1[O:15][C:16](=[O:20])[O:17][C:18]=1[CH3:19])=[O:11])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 19036162Tritylolmesartan medoxomil

Product 1

HCID 178440075HCID 178440075, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.4 g of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (a) above] and 48 ml of 75% v/v aqueous acetic acid was stirred at 60° C. for 1 hour, after which it was concentrated by evaporation under reduced pressure. The residue was dissolved in toluene, and the resulting solution was concentrated by distillation under reduced pressure; this was repeated a further time in order to remove the remaining water and acetic acid. The residue thus obtained was purified by column chromatography through silica gel using 1:9 and 1:4 by volume mixtures of methanol and methylene chloride as the eluent, to give 0.73 g of the title compound, melting at 170°-172° C.

Workup

  1. concentrationafter which it was concentrated by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in toluene
  3. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  4. customto remove the remaining water and acetic acid
  5. customThe residue thus obtained
  6. customwas purified by column chromatography through silica gel using 1:9 and 1:4 by volume mixtures of methanol and methylene chloride as the eluent

Sources & evidence

ORD record
ord-d81f12a09c4c4e0ca9f93ee1bd9d8e77
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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