Hydrochloric Acid → HCID 69871741, compound

HRID 1358568Notes

Reaction equation

HRID 1358568 reaction equation
C[O:2][C:3](=[O:49])[C@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[N:33]([CH3:34])[C:32]3[CH:35]=[C:36]([O:39][C:40]4[CH:45]=[C:44]([CH3:46])[C:43]([NH2:47])=[C:42]([CH3:48])[CH:41]=4)[CH:37]=[CH:38][C:31]=3[N:30]=2)=[CH:23][CH:22]=1)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[OH-].[Li+].[ClH:53].Cl.O1CCOCC1>O1CCCC1.O>[ClH:53].[ClH:53].[NH2:47][C:43]1[C:42]([CH3:48])=[CH:41][C:40]([O:39][C:36]2[CH:37]=[CH:38][C:31]3[N:30]=[C:29]([CH2:28][O:27][C:24]4[CH:23]=[CH:22][C:21]([CH2:20][C@@H:4]([C:3]([OH:49])=[O:2])[NH:5][C:6]5[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=5[C:12](=[O:19])[C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)=[CH:26][CH:25]=4)[N:33]([CH3:34])[C:32]=3[CH:35]=2)=[CH:45][C:44]=1[CH3:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 204431481,4-Dioxane hydrochlorideHCID 69871390HCID 69871390, compound

Product 1

HCID 69871741HCID 69871741, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]-N-(2-benzoylphenyl)phenylalanine methyl ester (0.25 g), lithium hydroxide monohydrate (0.04 g), tetrahydrofuran (5 ml) and water (2 ml) was stirred at room temperature for 3 hours. The reaction mixture was neutralized with 1N hydrochloric acid and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was chromatographed on LiChroprepDIOL (Merck) using ethyl acetate as the eluant to give a yellow material. To a solution of the material in tetrahydrofuran (3 ml) was added 4N hydrogen chloride/dioxane (1 ml) to give crystals. The crystals were isolated by filtration to afford the title compound (0.11 g, mp 148-155° C.).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe extract was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on LiChroprepDIOL (Merck)
  6. customto give a yellow material
  7. customto give crystals
  8. customThe crystals were isolated by filtration

Sources & evidence

ORD record
ord-fd23a4d78a9c4c439ebf0e0b92249af1
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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