Ethyl bromopyruvate → HCID 54238301, compound

HRID 842754Notes

Reaction equation

HRID 842754 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7][CH2:8][C:9]([NH2:11])=[S:10])(=[O:4])=[O:3].Br[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CCO>[CH2:18]([O:17][C:15]([C:14]1[N:11]=[C:9]([CH2:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[S:10][CH:13]=1)=[O:16])[CH3:19]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvate2×HCID 22246906HCID 22246906, compound

Product 1

HCID 54238301HCID 54238301, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methanesulfonylamino-thiobutyramide (0.35 g, 1.8 mmol) and ethyl bromopyruvate (0.37 g, 1.9 mmol) in EtOH (50 mL) was stirred at room temperature for 17 h. Additional ethyl bromopyruvate (0.05 g, 0.26 mmol) was added and the reaction mixture was stirred at room temperature for 5.5 h. The reaction mixture was concentrated and was purified by flash chromatography (79:1 to 19:1 EtOAc:MeOH) to afford the tile compound (0.47 g). 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 4.40 (q, 2H), 3.24 (t, 2H), 3.17 (t, 2H), 2.96 (s, 3H), 2.10 (t, 2H), 1.39 (t, 3H); MS 293 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas purified by flash chromatography (79:1 to 19:1 EtOAc:MeOH)

Sources & evidence

ORD record
ord-5f4ce513501e47088db4b546ffaeef0f
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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