Hydrochloric Acid → HCID 58136684, compound

HRID 877266Notes

Reaction equation

HRID 877266 reaction equation
[C:1]([C:5]1[O:6][CH2:7][C:8](=[O:40])[N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[C:19]([NH:21][C:22]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:23]=3[CH2:24][CH:25]([C:31]([O:33]C)=[O:32])[CH2:26]4)=[O:20])=[CH:14][CH:13]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1.O>[C:1]([C:5]1[O:6][CH2:7][C:8](=[O:40])[N:9]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[C:19]([NH:21][C:22]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:23]=3[CH2:24][CH:25]([C:31]([OH:33])=[O:32])[CH2:26]4)=[O:20])=[CH:16][CH:17]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58136512HCID 58136512, compound

Product 1

HCID 58136684HCID 58136684, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

167 mg (0.306 mmol) of methyl 4-{[{4-[(2-tert-butyl-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}(cyclopentyl)acetyl]amino}-2,3-dihydro-1H-indene-2-carboxylate (Example 108A) were dissolved in 14 ml of dioxane/water (3:1 v/v), and 0.46 ml of 1 N aqueous sodium hydroxide solution was added. The mixture was stirred at room temperature overnight. The mixture was then acidified with 1 N hydrochloric acid and extracted repeatedly with dichloromethane, and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC. This gave 68 mg (42% of theory) of the title compound as a mixture of diastereomers.

Workup

  1. extractionextracted repeatedly with dichloromethane
  2. washthe combined organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by preparative HPLC
  6. additionThis gave 68 mg (42% of theory) of the title compound as a mixture of diastereomers

Sources & evidence

ORD record
ord-f5c950c722f94115b6c46aecf8436526
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

Loading…