Ethyl bromoacetate → HCID 14856507, compound

HRID 1073333Notes

Reaction equation

HRID 1073333 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([F:15])=[CH:9][CH:10]=3)[CH:5]([S:16]([NH2:19])(=[O:18])=[O:17])[C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[K+].[Br-]>CN(C)C=O.O>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:5]1([S:16]([NH2:19])(=[O:17])=[O:18])[C:6]2[CH:7]=[C:8]([F:15])[CH:9]=[CH:10][C:11]=2[C:12]2[C:4]1=[CH:3][C:2]([F:1])=[CH:14][CH:13]=2)[CH3:28]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 253877Potassium BromideHCID 14856506HCID 14856506, compound

Product 1

HCID 14856507HCID 14856507, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, (26) (2.4 g, 8.5 mmoL) was added portionwise to a stirred suspension of sodium hydride (427 mg of a 60% dispersion in mineral oil, 1.25 eq) in dry dimethylformamide (60 mL , from CaH2). After 15 min, ethyl bromoacetate (1.8 g, 10.0 mmoL, 1.25 eq) was added and the mixture was stirred for an additional hour before it was diluted with water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (3×200 mL), dried (MgSO4), and concentrated. The residue was recrystallized from ethyl acetate/hexane to provide 1.5 g. A sample recrystallized a second time from ethyl acetate/hexane provided the following data: mp 215°-217° C.; IR (KBr) 3357, 3250, 1710, 1160, 828 cm-1 ; 1H NMR (CDCl3, 200 MHz) 7.65 (dd, 2H, J=4.8, 8.6Hz), 7.52 (ddd, 2 H, J= 2.5, 9.3Hz), 7.20 (ddd, 2H, J=2.3, 8.6, 8.6Hz), 3.97 (bs, 2H, exchangeable), 3.75 (q, 2H, J=7.1H), 0.85 (t, 3H, J=7.1Hz); MS m/z 367 (M+), 215 (base peak).

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with brine (3×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate/hexane
  6. customto provide 1.5 g
  7. customA sample recrystallized a second time from ethyl acetate/hexane
  8. customprovided the following data

Sources & evidence

ORD record
ord-a4b5e8c5898d476c88bb13edf9747c5f
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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