Ethyl bromopyruvate → HCID 54238301, compound

HRID 2298203Notes

Reaction equation

HRID 2298203 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 title 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-2f7b2c9854a542129a767e7d68c1cd64
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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