Hydrochloric Acid → HCID 11713948, compound

HRID 2194309Notes

Reaction equation

HRID 2194309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]1[N:35]=[C:36]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:37][C:38]=1[CH3:39])[CH2:6][N:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:20][C@@H:21]([CH2:27][CH3:28])[C:22]([O:24]CC)=[O:23])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.[OH-].[Na+].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]1[N:35]=[C:36]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:37][C:38]=1[CH3:39])[CH2:6][N:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:20][C@@H:21]([CH2:27][CH3:28])[C:22]([OH:24])=[O:23])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59571721HCID 59571721, compound

Product 1

HCID 11713948HCID 11713948, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

440 mg of ethyl (S)-(+)-2-{9-[3-methoxy-4-(5-methyl-2-phenyl-oxazole-4-ylmethoxy)-benzyl]-9H-carbazole-4-yloxy}butyrate was suspended in ethanol (4.4 mL), 175 μL of 5 N sodium hydroxide solution was added thereto, and stirred at room temperature for 4 hours. The reaction mixture was diluted with water, and adjusted to pH3 with 1 N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, and 420 mg of the subject compound was prepared as white solid. Optical purity 95% ee (HPLC).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo, and 420 mg of the subject compound
  6. customwas prepared as white solid

Sources & evidence

ORD record
ord-03b4778814a348debb4a37d89ed24032
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

Loading…