Hydrochloric Acid → HCID 22175672, compound

HRID 1797690Notes

Reaction equation

HRID 1797690 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[S:17][C:18]([C:22]([O:24]CC)=[O:23])=[C:19]([CH3:21])[N:20]=3)[CH:14]=2)[C:9](=[O:27])[N:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:7]=1[CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O.Cl>O1CCCC1.C(O)C>[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[S:17][C:18]([C:22]([OH:24])=[O:23])=[C:19]([CH3:21])[N:20]=3)[CH:14]=2)[C:9](=[O:27])[N:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:7]=1[CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22175509HCID 22175509, compound

Product 1

HCID 22175672HCID 22175672, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-butoxy-3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl)-4-methyl-1,3-thiazole-5-carboxylate (0.91 g, 1.6 mmol) in tetrahydrofuran (5 ml) and ethanol (5 ml) was added 1N sodium hydroxide solution (3 ml). The resulting mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crystals were recrystallized from ethyl acetate-diisopropyl ether to give 2-(4-butoxy-3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl)-4-methyl-1,3-thiazole-5-carboxylic acid (0.78 g, 89.7%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-b792364ed0df4979bf8f00747fe83f4f
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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