Diethyl Oxalate → HCID 135848643, compound

HRID 348105Notes

Reaction equation

HRID 348105 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[CH2:11]([O:18][CH2:19][C:20]([O:22]CC)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Cl.[CH3:28][S:29][CH2:30][CH2:31][O:32][CH:33]([CH3:37])[C:34]([NH2:36])=[NH:35].[O-]CC.[Na+]>O1CCCC1.C(O)C>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[NH:36][C:34]([CH:33]([O:32][CH2:31][CH2:30][S:29][CH3:28])[CH3:37])=[N:35][C:2]=1[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 2723922Sodium ethoxideHCID 21069791HCID 21069791, compound

Product 1

HCID 135848643HCID 135848643, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl oxalate (5.66 g, 38.7 mmol) and ethyl benzyloxyacetate (7.52 g, 38.7 mmol) in dry tetrahydrofuran (60 ml) were treated at 22° C. with sodium hydride (1.70 g of a 60% dispersion in mineral oil, 42.5 mmol) and the condensation product was reacted with a mixture of intermediate 11, 2-(2-(methylthio)ethoxy)propanamidine hydrochloride salt, (7.70 g, 38.7 mmol) in a solution of sodium ethoxide (19.3 mmol, prepared from 0.445 g of sodium) in ethanol (50 ml) to give 2.29 g (15% yield) of the title ester as a clear oil after chromatography on silica gel. 1HNMR 400 MHz (CDCl3) δ ppm: 1.33 (3H, t, J=7.1 Hz, CH3), 1.54 (3H, d, J=7.1 Hz, CH3), 2.16 (3H, s, SCH3), 2.7–2.8 (2H, m, CH2), 3.54 (1H, m, CH), 3.86 (1H, m, CH), 4.37 (2H, q, J=7.1 Hz, OCH2), 4.47 (1H, q, J=7.1 Hz, OCH), 5.34 (2H, ABq, JAB=11.0 Hz, OCH2), 7.37 (3H, m, aromatics), 7.49 (2H, m, aromatics). MS (ESI+) m/z 393 [M+H+].

Sources & evidence

ORD record
ord-95f2cc46c66348b69ec36a2cd77c9210
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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