Formic Acid → Candesartan Cilexetil

HRID 640738Notes

Reaction equation

HRID 640738 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.C(O)=O>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

6

Reactant 4

HCID 284Formic AcidHCID 887MethanolHCID 1140TolueneHCID 11029254Trityl candesartan cilexetil

Product 1

HCID 2540Candesartan Cilexetil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of trityl candesartan cilexetil (TCC, 30.0 g, 35.17 mmol), toluene (180 mL), methanol (180 mL), formic acid (1.6 g) and water (0.63 g) was refluxed for about 10 h (HPLC control), the solvents were evaporated at 60° C./30 mbar to give a residue as a viscous oil, (about 31 g, theoretical yield of candesartan cilexetil is 21.47 g).

Workup

  1. customthe solvents were evaporated at 60° C./30 mbar

Sources & evidence

ORD record
ord-5978dd493bde4222a2481041160b1575
Source dataset
uspto-grants-2010_04
Patent number
US07692023B2

Reaction notes

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