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

HRID 326723Notes

Reaction equation

HRID 326723 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 ambient temperature. After stirring at ambient temperature for 16 hours, the mixture was filtered and concentrated to dryness. The residue was chromatographed on silica gel eluted with 10% MeOH in CHCl3 /hexane (1:1→2:1) to give 0.98 g of the title compound. TLC Rf=0.61 (10%MeOH/CHCl3). MS(DCl) m/e 333 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.25(t, J=7.4 Hz, 3H), 1.30(t, J=7.4 Hz,3H), 4.13(s,2H), 4.18(q, J=7.4 Hz,2H), 4.28(q, J=7.4 Hz,2H), 4.28(q, J=7.4 Hz,2H), 4.30(s,2H), 6.92(br s, 1H), 6.98(d, J=7.4 Hz, 1H), 7.12(t, J=7.4 Hz, 1H), 7.26(d,J=7.4 Hz, 1H), 8.03(br s, --OH), 8.17 (br s, --NH).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated to dryness
  3. customThe residue was chromatographed on silica gel
  4. washeluted with 10% MeOH in CHCl3 /hexane (1:1→2:1)

Sources & evidence

ORD record
ord-f36c214b4e6d42f3b1b1cd15633ec735
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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