Ethyl bromopyruvate → HCID 45117587, compound

HRID 1009201Notes

Reaction equation

HRID 1009201 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=[S:12])[NH2:11])[CH3:9])(C)(C)C.Br[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH2:20]([O:19][C:17]([C:16]1[N:11]=[C:10]([CH:8]([NH2:7])[CH3:9])[S:12][CH:15]=1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 5365025tert-butyl N-(1-carbamothioylethyl)carbamate

Product 1

HCID 45117587HCID 45117587, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1-Thiocarbamoyl-ethyl)-carbamic acid tert-butyl ester (8.7 g, 42.5 mmol) and ethyl bromopyruvate (90% Tech., 9.21 g, 42.5 mmol) were heated at reflux in ethanol (200 mL) for 12 hours. The ethanol was removed in vacuo and the residue was purified by flash chromatography (5:95 MeOH:CH2Cl2) to afford the title compound (1.24 g, 15% over two steps): 1H NMR (400 MHz, d6-DMSO): 8.37 (s, 1H), 4.28 (qd, 2H), 4.24 (q, 1H), 2.60 (br s, 2H), 1.37 (d, 3H), 1.29 (t, 3H); MS (ESI-LCMS) for C8H13N2O2S: 201 (MH+).

Workup

  1. customThe ethanol was removed in vacuo
  2. customthe residue was purified by flash chromatography (5:95 MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-b81e656c6c1146239751f5bfe477521e
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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