Ethyl bromoacetate → HCID 11234214, compound

HRID 1354076Notes

Reaction equation

HRID 1354076 reaction equation
[OH:1][CH2:2][CH:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].CCN(CC)CC.Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:38]([O:37][C:35]([CH2:34][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH:3]([CH2:2][OH:1])[C:4]([O:6][CH3:7])=[O:5])=[O:36])[CH3:39]

Participants

8

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Product 1

HCID 11234214HCID 11234214, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 1 (5.65 g, 19.5 mmol) and anhydrous potassium carbonate anhydrous (8 g, 60 mmol) were suspended in DMF (35 mL), a catalytic amount of Et3N was introduced, and ethyl bromoacetate (4.3 mL, 40 mmol) was added dropwise. After stirring for 5 hours, 50 mL of distilled water and 100 mL of ethyl acetate were introduced and stirred to separate layers. The supernatant was washed with a 1N HCl aqueous solution (50 mL), a saturated NaHCO3 aqueous solution (50 mL), and distilled water (100 mL), and it was dried and concentrated under reduced pressure. The mixture was separated using hexane and ethylacetate (2:1) in a silica gel column to obtain a yellow thick oily title compound (5.26 g, yield 72%).

Workup

  1. stirringstirred
  2. customto separate layers
  3. washThe supernatant was washed with a 1N HCl aqueous solution (50 mL)
  4. distillationa saturated NaHCO3 aqueous solution (50 mL), and distilled water (100 mL), and it
  5. customwas dried
  6. concentrationconcentrated under reduced pressure
  7. customThe mixture was separated

Sources & evidence

ORD record
ord-b2997a760b5b487db3dcc23887b60db2
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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