Sodium Carbonate → Ethyl alpha-(hydroxyimino)-beta-(4-(carboethoxymethyl)indol-3-yl)-propanoate

HRID 1742752Notes

Reaction equation

HRID 1742752 reaction equation
[C:1]([CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)([O:3][CH2:4][CH3:5])=[O:2].Br[CH2:17][C:18](=[N:24][OH:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[OH:25][N:24]=[C:18]([CH2:17][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[CH:15][C:7]=2[CH2:6][C:1]([O:3][CH2:4][CH3:5])=[O:2])[NH:11][CH:10]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12721920ethyl 2-(1H-indol-4-yl)acetateHCID 53428735Ethyl 3-bromo-2-(hydroxyimino)propanoate

Product 1

HCID 131718262Ethyl alpha-(hydroxyimino)-beta-(4-(carboethoxymethyl)indol-3-yl)-propanoateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(carboethoxymethyl)indole (830 mg, 4.12 mmol) and ethyl bromopyruvate 2-oxime (866 mg, 4.12 mmol) in methylene chloride (40 mL) was added anhydrous Na2CO3 (2.40 g, 22.66 mmol) at room temperature. After stirring at room temperature for 16 hours, the mixture was filtered and concentrated to dryness. The residue was flash chromatographed on silica gel (eluting (10% MeOH/CHCl3):hexane=1:1→2:1) to give 0.98 g of the title compound; TLC Rf =0.61 (10% MeOH/CHCl3). MS(CI) m/e 333 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ8.17 (br s, --NH), 8.03 (br s, --OH), 7.26 (d, J=7.4 Hz, 1H), 7.12 (t, J=7.4 Hz, 1H), 6.98 (d, J=7.4 Hz, 1H) 6.92 (br s, 1H), 4.30 (s, 2 H), 4.28 (q, J=7.4 Hz, 2H), 4.18 (q, J=7.4 Hz, 2H), 4.13 (s, 2H), 1.30 (t, J=7.4 Hz, 3H), 1.25 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated to dryness
  3. customchromatographed on silica gel (eluting (10% MeOH/CHCl3):hexane=1:1→2:1)

Sources & evidence

ORD record
ord-2b90b7e18a8a454291bde6d4c962371b
Source dataset
uspto-grants-1994_08
Patent number
US05340802

Reaction notes

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