Lithium Hydroxide → HCID 178447278, compound

HRID 2220147Notes

Reaction equation

HRID 2220147 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=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)C=CC=CC=1.[OH-].[Li+]>C(O)(=O)C.O.O1CCOCC1.O>[NH:10]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[CH:21][C:22]([CH2:25][N:26]([C:33]3[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=3)[C:36]([OH:38])=[O:37])[C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:24]=2)=[N:12][N:8]=[N:9]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23134769HCID 23134769, compound

Product 1

HCID 178447278HCID 178447278, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 218864351,4-Dioxane--water (1/1)SolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

Ethyl 3-[N-[[4-[2-(3-triphenylmethyl-3H-tetrazol-5-yl)phenyl]phenyl]methyl]-N-pentanoylamino]benzoate (0.37 g) synthesized in Example 1a was dissolved in 75% acetic acid-water (8.8 ml), and the mixture was stirred at room temperature for 24 hrs. The reaction mixture was concentrated and dried to give a solid. The residue was dissolved in 75% dioxane-water (8.8 ml), lithium hydroxide (45 mg) was added, and the mixture was stirred at 50° C. for 24 hrs. The reaction mixture was concentrated to give a solid, and the residue was purified by silica gel column chromatography (methylene chloride-methanol:7-3 v/v) to give the object compound (0.12 g, yield 88%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried
  3. customto give a solid
  4. stirringthe mixture was stirred at 50° C. for 24 hrs
  5. concentrationThe reaction mixture was concentrated
  6. customto give a solid
  7. customthe residue was purified by silica gel column chromatography (methylene chloride-methanol:7-3 v/v)

Sources & evidence

ORD record
ord-05e131a8d8c64b76a2d2341b6bd3ab60
Source dataset
uspto-grants-2008_08
Patent number
US07417052B2

Reaction notes

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