Hydrochloric Acid → 2-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}-2-methyl-propionic acid

HRID 2194300Notes

Reaction equation

HRID 2194300 reaction equation
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[C:6]([O:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1.Cl[CH2:24][C:25]1[CH:44]=[CH:43][C:28]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:34][C:35]=2[CH3:36])=[C:27]([O:45][CH3:46])[CH:26]=1.Cl>O.CN(C)C=O>[CH3:46][O:45][C:27]1[CH:26]=[C:25]([CH:44]=[CH:43][C:28]=1[O:29][CH2:30][C:31]1[N:32]=[C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:34][C:35]=1[CH3:36])[CH2:24][N:14]1[C:15]2[CH:3]=[CH:4][CH:5]=[C:6]([O:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19])[C:7]=2[C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 223446094-(4-Chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 595717422-(9H-carbazole-4-yloxy)-2-methylpropionic acid

Product 1

HCID 117211692-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}-2-methyl-propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

302 mg of sodium hydride (60%) was added to N,N-dimethylformamide (30 mL) solution of 924 mg of 2-(9H-carbazole-4-yloxy)-2-methylpropionic acid, stirred at room temperature for 20 minutes. Thereafter, 1.31 g of 4-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-5-methyl-2-phenyloxazole was added thereto, and stirred at room temperature for 1 hour. The reaction mixture was poured into water, adjusted to pH3 with 1 N hydrochloric acid, and extracted twice with ethyl acetate. The combined extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the residue was purified by silica gel chromatography (chloroform:methanol=50:1), and 1.88 g of the subject compound was prepared as pale yellow powder.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. extractionextracted twice with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel chromatography (chloroform:methanol=50:1), and 1.88 g of the subject compound
  9. customwas prepared as pale yellow powder

Sources & evidence

ORD record
ord-e1633d0a59734018b06d713bf99df20c
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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