Water → HCID 178440075, compound

HRID 52985Notes

Reaction equation

HRID 52985 reaction equation
O.[OH:2][C:3]([C:6]1[N:7]=[C:8]([CH2:59][CH2:60][CH3:61])[N:9]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:39](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[O:16][C:17](=[O:21])[O:18][C:19]=1[CH3:20])=[O:12])([CH3:5])[CH3:4]>C(O)(=O)C>[OH:2][C:3]([C:6]1[N:7]=[C:8]([CH2:59][CH2:60][CH3:61])[N:9]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[O:16][C:17](=[O:21])[O:18][C:19]=1[CH3:20])=[O:12])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 962Water2×HCID 19036162Tritylolmesartan medoxomil

Product 1

HCID 178440075HCID 178440075, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

75 ml of water were added to a suspension of 29.3 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] in 225 ml of acetic acid, and the resulting mixture was stirred at 60° C. for 1.5 hours. At the end of this time, 75 ml of water were added to the mixture, which was then cooled. Precipitated trityl alcohol was removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. Toluene was added to the residue, and the mixture was again concentrated by evaporation under reduced pressure, to remove the remaining water and acetic acid. The residue was crystallized in ethyl acetate, to give 16.6 g of the title compound as crystals, melting at 177°-180° C. (with decomposition).

Workup

  1. temperaturewas then cooled
  2. customPrecipitated trityl alcohol was removed by filtration
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. additionToluene was added to the residue
  5. concentrationthe mixture was again concentrated by evaporation under reduced pressure
  6. customto remove the remaining water and acetic acid
  7. customThe residue was crystallized in ethyl acetate

Sources & evidence

ORD record
ord-bdc575ab3f854786820802ad88a3b6ba
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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