Ethyl bromoacetate → HCID 70025487, compound

HRID 1264534Notes

Reaction equation

HRID 1264534 reaction equation
[H-].[Na+].[C:3]1([CH2:13][NH:14][C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][N:14]([CH2:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[C:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=1)[CH3:32]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 18612695HCID 18612695, compound

Product 1

HCID 70025487HCID 70025487, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Charged flask with a 60% sodium hydride in oil dispersion (64.0 mg, 1.6 mmol) and suspended in DMF (1 ml). A DMF (1 ml) solution of naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)-amine (300 mg, 1.0 mmol ) was added and the mixture stirred under argon at rt for 30 min resulting in a light yellow solution. After adding ethyl bromoacetate (333 μl, 3.0 mmol), the reaction was stirred at rt for 1 hr, poured into 10% sodium bicarbonate (aq) and extracted with ethyl acetate (3×). The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a crude oil (370 mg). Flash chromatography on silica gel (15% ethyl acetate in hexane) gave the title compound as a colorless oil (306 mg, 73.9%).

Workup

  1. customresulting in a light yellow solution
  2. stirringthe reaction was stirred at rt for 1 hr
  3. extractionextracted with ethyl acetate (3×)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude oil (370 mg)

Sources & evidence

ORD record
ord-007ce9f623e645e49fad04de63de330f
Source dataset
uspto-grants-2003_04
Patent number
US06544982B1

Reaction notes

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