Dimethylformamide → HCID 58492458, compound

HRID 68145Notes

Reaction equation

HRID 68145 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:29](=[O:30])[C:28]3[C:19](=[C:20]([O:31][CH2:32][CH2:33][CH3:34])[CH:21]=[C:22]4[C:27]=3[O:26][CH2:25][CH2:24][CH2:23]4)[NH:18][CH:17]=2)=[CH:12][CH:11]=1.Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>C(OCC)(=O)C.O>[CH2:40]([O:39][C:37](=[O:38])[CH2:36][N:18]1[C:19]2[C:28](=[C:27]3[C:22](=[CH:21][C:20]=2[O:31][CH2:32][CH2:33][CH3:34])[CH2:23][CH2:24][CH2:25][O:26]3)[C:29](=[O:30])[C:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:15][CH:14]=2)=[CH:17]1)[CH3:41]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 46224430HCID 46224430, compound

Product 1

HCID 58492458HCID 58492458, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil base, 80 mg, 2.0 mmol) was added to a DMF solution (10 ml) of 3-(4-methoxyphenyl)-10-propoxy-1,6,7,8-tetrahydro-5-oxa-1-aza-phenanthren-4-one (600 mg, 1.64 mmol), the resulting mixture was then stirred at room temperature for 5 minutes. Ethyl bromoacetate (330 mg, 2.0 mmol) was added thereto and the resulting mixture was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using medium pressure liquid chromatography (NH silica gel, n-hexane:ethyl acetate=100:0→0:100). The purified product was concentrated under reduced pressure, giving a colorless oily substance ethyl[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetate (700 mg, yield: 95%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. customfollowed by separation
  3. washThe thus-obtained organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24ff477c705941949a723770fa84a8d6
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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