Sodium Hydroxide → HCID 23134795, compound

HRID 2220148Notes

Reaction equation

HRID 2220148 reaction equation
[C:1]1([C:7]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]([C:33]4[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=4)[C:36]([O:38]CC)=[O:37])[C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:21][CH:20]=3)[N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCOCC1>[C:44]1([C:7]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]([C:33]4[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=4)[C:36]([OH:38])=[O:37])[C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:21][CH:20]=3)[N:10]=[N:9]2)[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23134769HCID 23134769, compound

Product 1

HCID 23134795HCID 23134795, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-[N-[[4-[2-(3-triphenylmethyl-3H-tetrazol-5-yl)phenyl]phenyl]methyl]-N-pentanoylamino]benzoate (11.50 g) synthesized in Example 1a in dioxane (100 ml) was added 1N-aqueous sodium hydroxide solution (19 ml), and the mixture was stirred at room temperature for 5 days. The reaction mixture was concentrated, ethyl acetate and saturated aqueous potassium bisulfate solution were added to carry out partitioning and extraction. The extracted organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtrated and concentrated to give a crude product of 3-[N-[[4-[2-(3-triphenylmethyl-3H-tetrazol-5-yl)phenyl]phenyl]methyl]-N-pentanoylamino]benzoic acid. To a solution of the obtained crude product in DMA (90 ml) were added potassium carbonate (4.86 g) and a solution of 4-chloromethyl-5-methyl-1,3-dioxolen-2-one (3.92 g) in DMA (5 ml), and the mixture was stirred at room temperature for 24 hrs. The reaction mixture was poured into ethyl acetate-water to carry out partitioning and extraction. The extracted organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtrated and concentrated, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate:1-1 v/v) to give (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl3-[N-[[4-[2-(3-triphenylmethyl-3H-tetrazol-5-yl)phenyl]phenyl]methyl]-N-pentanoylamino]benzoate (11.57 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate and saturated aqueous potassium bisulfate solution were added
  3. customto carry out partitioning
  4. extractionextraction
  5. washThe extracted organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ec9a6c588a6f49048c00cc6b555b88cd
Source dataset
uspto-grants-2008_08
Patent number
US07417052B2

Reaction notes

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