Ethyl bromopyruvate → HCID 9967188, compound

HRID 895711Notes

Reaction equation

HRID 895711 reaction equation
[SH:1][C:2]1[Se:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CC#N.ClCCl>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH2:12][S:1][C:2]1[Se:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1)[CH3:18]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 178527780HCID 178527780, compound

Product 1

HCID 9967188HCID 9967188, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-mercaptobenzselenazole (418 mg, 2 mmol) in 4 mL of MeCN and 4 mL of dichloromethane with vigorous stirring was added dropwise, ethyl bromopyruvate (290 mg, 2 mmol). The resulting mixture was stirred for 5 h. It was allowed to settle for 30 min and then filtered. The solid was washed with EtOAc/hexanes (1:1, 2×8 mL) and dried in high vacuum to afford 3-(benzoselenazol-2-ylsulfanyl)-2-oxo-propionic acid ethyl ester as a white powder (582 mg, 89%). 1H-NMR (DMSO-d6, 300 MHz) δ (ppm): 8.14-8.10 (m, 1H), 7.95-7.92 (m, 0.7H), 7.75-7.73 (m, 0.3H), 7.52-7.45 (m, 1H), 7.36-7.30 (m,1H), 7.07 (s, 0.7H), 4.69 (s, 0.6), 4.37-4.27 (m, 2H), 1.32 (t, J=7 Hz, 3H). MS(ESI) m/z: 330(M+H+, 55), 348 M++H2O, 58), 362 (M++MeOH, 100).

Workup

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred for 5 h
  3. filtrationfiltered
  4. washThe solid was washed with EtOAc/hexanes (1:1, 2×8 mL)
  5. customdried in high vacuum

Sources & evidence

ORD record
ord-d76d95e7e21247d28a53608e3c14c260
Source dataset
uspto-grants-2005_07
Patent number
US06916850B2

Reaction notes

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