Acetate → HCID 21103279, compound

HRID 1354083Notes

Reaction equation

HRID 1354083 reaction equation
[OH:1][CH2:2][CH:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].O.C([O-])(=O)C>CN(C=O)C>[CH2:26]([O:25][C:23]([CH2:22][N:8]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)(=[O:10])=[O:11])[CH:3]([CH2:2][OH:1])[C:4]([O:6][CH3:7])=[O:5])=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 175AcetateHCID 962WaterHCID 7748Ethyl bromoacetateHCID 11185781HCID 11185781, compound

Product 1

HCID 21103279HCID 21103279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-hydroxy-2-(4-nitro-benzenesulfonylamino)-propionate (4.0 g, 13.1 mmol) and potassium carbonate anhydride (5.45 g, 39.4 mmol) were suspended in DMF (25 mL), and ethyl bromoacetate (2.91 mL, 26.3 mmol) was added dropwise at 0° C. After stirring for 4 hours, 50 mL of distilled water and 100 mL of acetate were introduced and stirred to separate layers. The supernatant was washed with 50 mL of a 5% Na2S2O3 aqueous solution, 50 mL of a 1N HCl aqueous solution, 50 mL of a saturated NaHCO3 aqueous solution, and 100 mL of distilled water, and it was dried and concentrated under reduced pressure. The mixture was separated with hexane and ethylacetate (2:1) in a silica gel column to obtain a yellow oil (4.43 g, 86.5).

Workup

  1. stirringstirred
  2. customto separate layers
  3. washThe supernatant was washed with 50 mL of a 5% Na2S2O3 aqueous solution, 50 mL of a 1N HCl aqueous solution, 50 mL of a saturated NaHCO3 aqueous solution, and 100 mL of distilled water, and it
  4. customwas dried
  5. concentrationconcentrated under reduced pressure
  6. customThe mixture was separated with hexane and ethylacetate (2:1) in a silica gel column
  7. customto obtain a yellow oil (4.43 g, 86.5)

Sources & evidence

ORD record
ord-25813896e28b40c48c7d4cf4980e165c
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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