Ethyl bromoacetate → HCID 14856495, compound

HRID 1073324Notes

Reaction equation

HRID 1073324 reaction equation
[H-].[Na+].[CH:3]1[C:15]2[CH:14]([S:16]([NH2:19])(=[O:18])=[O:17])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O.O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:14]1([S:16]([NH2:19])(=[O:17])=[O:18])[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[C:15]1=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:26]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14856494HCID 14856494, compound

Product 1

HCID 14856495HCID 14856495, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a stirred, 15° C. suspension of sodium hydride (60% in mineral oil, 500 mg, 12.2 mmoL, 1 eq) in 50 mL of dry dimethylformamide (from molecular sieves) under nitrogen was added dropwise over 15 minutes a solution of (8) (3 g, 12.2 mmoL) in 100 mL of dimethylformamide. A solution of ethyl bromoacetate (2.0 g, 12.2 mmoL, 1 eq) in 20 mL of dimethylformamide was then added dropwise over 10 minutes. After 3 h at room temperature, the reaction was diluted with water (100 mL), acidified (pH 5) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine (5×100 mL), dried (MgSO4), filtered and evaporated. The crude oil was purified by chromatography on silica gel using a gradient of 10%-30% ethyl acetate in hexane to provide 1 g (25%) of product: mp 167°-170° C., 1H NMR (CDCl3) 7.8-7.2 (m, 8H, aromatic protons), 3.9 (broad single, 2H), 3.6 (s, 2H), 3.5 (q, 2H), 1.7 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic extracts were washed with brine (5×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude oil was purified by chromatography on silica gel using a gradient of 10%-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8d3d7f8ba2f645c88650225f4f65acef
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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