Ethyl bromoacetate → HCID 59651901, compound

HRID 2042572Notes

Reaction equation

HRID 2042572 reaction equation
[H-].[Na+].[CH3:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:27])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:15][CH:14]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CS(C)=O.C1(C)C=CC=CC=1>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][CH:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][N:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[CH3:3])=[CH:14][CH:15]=1)=[O:27])[CH3:34]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 59651904HCID 59651904, compound

Product 1

HCID 59651901HCID 59651901, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 1140TolueneSolvent

Procedure

A mixture of sodium hydride (0.092 g, 3.8 mmoL) in 10 mL of DMSO was stirred under N2 as the product from step 3 (1.0 g, 3.8 mmol) in 5.0 mL of DMSO was added dropwise. After the reaction was stirred for 30 min, a solution of ethyl bromoacetate (0.64 g, 8.83 mmol) in 6.0 mL of toluene was added dropwise, and the reaction was stirred at rt for 1 h. The reaction was then quenched with NH4Cl solution and the solvent was evaporated. The residue was extracted with CH2Cl2 (3×20 mL), combined, washed with saturated NaHCO3, saturated NaCl then dried over Na2SO4. The crude product was purified by flash chromatography using 10% MeOH in CH2Cl2 to give the product (0.65 g, 52%).

Workup

  1. additionwas added dropwise
  2. stirringthe reaction was stirred at rt for 1 h
  3. customThe reaction was then quenched with NH4Cl solution
  4. customthe solvent was evaporated
  5. extractionThe residue was extracted with CH2Cl2 (3×20 mL)
  6. washwashed with saturated NaHCO3, saturated NaCl
  7. dry with materialthen dried over Na2SO4
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6171131cfec2461e8d5de1a53929f1f5
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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