Ethyl bromoacetate → HCID 54551452, compound

HRID 850481Notes

Reaction equation

HRID 850481 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:8])=[C:5]([N+:23]([O-:25])=[O:24])[C:4]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C1COCC1.[H-].[Na+].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>O>[CH2:44]([O:43][C:41](=[O:42])[CH2:40][N:9]([C:7](=[O:8])[C:6]1[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:5]=1[N+:23]([O-:25])=[O:24])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)[CH3:45]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetate2×HCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 19363428HCID 19363428, compound

Product 1

HCID 54551452HCID 54551452, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Methoxy-2-nitro-N-[2-(4nitrophenyl)ethyl]-3-pentyloxybenzamide obtained in Example 2-47, THF (1 ml) and sodium hydride (13.3 mg, 0.556 mmol) were mixed, and the mixture was stirred for 5 minutes. Ethyl bromoacetate (0.0617 ml, 0.556 mmol) was added, and the mixture was stirred at 90° C. for 5.5 hours. Then, sodium hydride (6.7 mg, 0.278 mmol) and ethyl bromoacetate (6.7 mg, 0.278 mmol) were further added, and the mixture was stirred at 90° C. for 6.5 hours. To the mixture was added water (3 ml) to stop the reaction, and the organic layer was extracted 3 times with ethyl acetate (5 ml). The organic layers were combined and dried over anhydrous magnesium sulfate. The drying agent was fitered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1-2/3) to give ethyl{ (4-methoxy-2-nitro-3-pentyloxybenzoyl)-[2-(4nitrophenyl)ethyl]amino}acetate (0.137 g, 68%) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at 90° C. for 5.5 hours
  2. stirringthe mixture was stirred at 90° C. for 6.5 hours
  3. customthe reaction
  4. extractionthe organic layer was extracted 3 times with ethyl acetate (5 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1-2/3)

Sources & evidence

ORD record
ord-35cb8213aa154d848d55a4e754d70575
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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