Methanol → Candesartan Cilexetil

HRID 11805Notes

Reaction equation

HRID 11805 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([C:26]4[N:30](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:29]=[N:28][N:27]=4)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:50]([O:52][CH:53]([O:55][C:56]([O:58][CH:59]2[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]2)=[O:57])[CH3:54])=[O:51])[N:5]=1.C1(C)C=CC=CC=1.CO>O>[CH3:1][CH2:2][O:3][C:4]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[N:27]=[N:28][NH:29][N:30]=3)=[CH:16][CH:15]=2)[C:11]2[C:10]([C:50]([O:52][CH:53]([O:55][C:56]([O:58][CH:59]3[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64]3)=[O:57])[CH3:54])=[O:51])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1140TolueneHCID 11029254Trityl candesartan cilexetil

Product 1

HCID 2540Candesartan Cilexetil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of trityl candesartan cilexetil (20 g, 23.45 mmol), toluene (60 ml), methanol (60 ml), and water (1 ml) was gently refluxed for about 12 h. The reaction was monitored by HPLC. The solution volume was reduced by evaporation under reduced pressure (30 mbar) at a temperature of about 55° C. 60° C. to obtain viscous oil of candesartan cilexetil as a residue (36.5 g).

Workup

  1. temperaturewas gently refluxed for about 12 h
  2. customThe solution volume was reduced by evaporation under reduced pressure (30 mbar) at a temperature of about 55° C

Sources & evidence

ORD record
ord-cf2755c8bda948af8d1a138c3269dbe4
Source dataset
uspto-grants-2006_08
Patent number
US07098342B2

Reaction notes

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