Sulfuric Acid → HCID 178440066, compound

HRID 1427702Notes

Reaction equation

HRID 1427702 reaction equation
O[C:2]([C:5]1[N:6]=[C:7]([CH2:39][CH2:40][CH3:41])[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].CN(C)C(=O)C.S(=O)(=O)(O)O.[OH-].[Na+]>C(Cl)Cl.O>[C:2]([C:5]1[N:6]=[C:7]([CH2:39][CH2:40][CH3:41])[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])=[CH2:3]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 178440075HCID 178440075, compound

Product 1

HCID 178440066HCID 178440066, compoundYield 116.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

(5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylate [olmesartan medoxomil] (20.0 g) was added into anhydrous N,N-dimethylacetamide (80 ml) under a nitrogen stream, and after dissolution was confirmed, concentrated sulfuric acid (3.0 ml) was poured in and the mixture was reacted at about 100° C. for 2.5 hours. Upon completion of the reaction, the reaction mixture was cooled to about 40° C. and poured into cold water (80 ml). After methylene chloride (80 ml) was poured in, the pH of the reaction mixture was adjusted to 4.2 with 25% sodium hydroxide. The organic layer was separated, washed with brine (80 ml) and concentrated under reduced pressure to obtain 22.58 g of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-isopropenyl-2-propyl-1-[[2′-[1H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate [crude olmesartan medoxomil dehydrate] as a foam.

Workup

  1. dissolutionafter dissolution
  2. customwas reacted at about 100° C. for 2.5 hours
  3. customUpon completion of the reaction
  4. customThe organic layer was separated
  5. washwashed with brine (80 ml)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-15885ab00f764a7382b24ae529fe3af6
Source dataset
uspto-grants-2015_01
Patent number
US08933241B2

Reaction notes

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