Ethyl bromopyruvate → HCID 9834577, compound

HRID 895705Notes

Reaction equation

HRID 895705 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(Cl)Cl>[CH2:13]([O:12][C:10](=[O:11])[C:9](=[O:15])[CH2:8][S:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1)[CH3:14]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 178527881HCID 178527881, compound

Product 1

HCID 9834577HCID 9834577, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-mercaptothiazole (238 mg, 2 mmol) and ethyl bromopyruvate (0.264 mL, 2.1 mmol) in methylene chloride (7 mL) was shaken at 20° C. for 3 hours under nitrogen. The obtained solid was filtered, washed with methylene chloride, and dried under vacuum. This gave the expected product, 3-(4,5-dihydro-thiazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester (440 mg, yield 71%) as a solid. 1H-NMR (300 Hz, D3COD) δ (ppm): 4.63 (d, J=13.1 Hz, 1H), 4.30-4.15 (m, 6H), 4.10 (d, J=13.1 Hz, 1H), 1.34 (t, J=7.1 Hz, 3H). MS (ESI) m/z: 234 (M+H, 100).

Workup

  1. filtrationThe obtained solid was filtered
  2. washwashed with methylene chloride
  3. customdried under vacuum

Sources & evidence

ORD record
ord-140596444109441bab8fca71c0eb9fe9
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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