Water → HCID 11234214, compound

HRID 1354075Notes

Reaction equation

HRID 1354075 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+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].O>CN(C=O)C>[CH2:31]([O:30][C:28]([CH2:27][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:29])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Product 1

HCID 11234214HCID 11234214, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 1 (7.2 g, 24.8 mmol) and anhydrous potassium carbonate (7 g, 50 mmol) were suspended in DMF (50 mL), and ethyl bromoacetate (4.5 Ml, 37 mmol) was added dropwise. After stirring for 40 hours, 50 ml of distilled water and 100 mL of ethyl acetated 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 (5.04 g, yield 54%).

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-bb36167028694b9d8a708bb3fdfff0ce
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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