Hydrochloric Acid → HCID 9917719, compound

HRID 1358562Notes

Reaction equation

HRID 1358562 reaction equation
[C:1]12([C:11]3[CH:50]=[CH:49][C:14]([O:15][C:16]4[CH:17]=[CH:18][C:19]5[N:23]=[C:22]([CH2:24][O:25][C:26]6[CH:31]=[CH:30][C:29]([CH2:32][CH:33]([O:38][CH2:39][C:40]7[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=7)[C:34]([O:36]C)=[O:35])=[CH:28][CH:27]=6)[N:21]([CH3:47])[C:20]=5[CH:48]=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>O.O1CCCC1.CO>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][C:16]4[CH:17]=[CH:18][C:19]5[N:23]=[C:22]([CH2:24][O:25][C:26]6[CH:31]=[CH:30][C:29]([CH2:32][CH:33]([O:38][CH2:39][C:40]7[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=7)[C:34]([OH:36])=[O:35])=[CH:28][CH:27]=6)[N:21]([CH3:47])[C:20]=5[CH:48]=4)=[CH:49][CH:50]=3)[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 10233544HCID 10233544, compound

Product 1

HCID 9917719HCID 9917719, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-[4-[6-(4-adamantan-1-ylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]phenyl]-2-(4-fluorobenzyloxy)propionate (0.25 g), aqueous 2N sodium hydroxide solution (2 ml) and methanol (5 ml) was stirred at room temperature for 2 hours. To the reaction mixture was added tetrahydrofuran (5 ml) and the mixture was stirred for 4 hours. The reaction mixture was poured into water and neutralized with hydrochloric acid and sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The ethyl acetate was evaporated under reduced pressure. The residue crystallized in ethyl acetate and the crystals were isolated by filtration to afford the title compound (0.23 g, mp 148-149° C.).

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ethyl acetate was evaporated under reduced pressure
  6. customThe residue crystallized in ethyl acetate
  7. customthe crystals were isolated by filtration

Sources & evidence

ORD record
ord-f5d5703c80844e54bce4406217a4c410
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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