Ethyl bromopyruvate → HCID 11349878, compound

HRID 1993801Notes

Reaction equation

HRID 1993801 reaction equation
[CH:1]1([NH:4][C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14]([NH2:16])=[S:15])[CH:7]=2)[CH2:3][CH2:2]1.Br[CH2:19][C:20](=O)[C:21]([O:23]CC)=O>C(O)C>[C:8]1([NH:13][C:21]([C:20]2[N:16]=[C:14]([NH:13][C:8]3[CH:7]=[C:6]([C:5](=[O:17])[NH:4][CH:1]4[CH2:3][CH2:2]4)[CH:11]=[CH:10][C:9]=3[CH3:12])[S:15][CH:19]=2)=[O:23])[CH:9]=[CH:10][CH:11]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 86595436HCID 86595436, compound

Product 1

HCID 11349878HCID 11349878, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of N-Cyclopropyl-4-methyl-3-thioureido-benzamide 3A (100 mg, 0.48 mmol) in 10 mL of ethanol was added ethyl bromopyruvate (89 mg, 0.48 mmol) and the reaction was heated at 75° C. overnight. After 16 hours, the reaction was cooled and concentrated and the crude product was purified by flash chromatography on silica gel loaded with CH2Cl2 and eluted with 1:1 hexanes/ethyl acetate followed by 1:2 hexanes/ethyl acetate to provide the title compound as a solid (75 mg, 45%). HPLC, tR, 2.97 min. (4 minute method); MS, m/z 346.0 [M+1]+.

Workup

  1. temperaturethe reaction was cooled
  2. concentrationconcentrated
  3. customthe crude product was purified by flash chromatography on silica gel
  4. washeluted with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-5b47b6545466413a9ea5a394be00ed3e
Source dataset
uspto-grants-2010_01
Patent number
US07652044B2

Reaction notes

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