Diethyl Oxalate → HCID 57565029, compound

HRID 1726907Notes

Reaction equation

HRID 1726907 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+].Br.[OH:28][CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][N:33]=[C:32]1[NH2:36]>>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[N:33]2[CH2:34][CH2:35][N:31]([CH2:30][CH2:29][OH:28])[C:32]2=[N:36][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

5

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 69027596HCID 69027596, compound

Product 1

HCID 57565029HCID 57565029, compoundYield 9.4%

Procedure

Reaction of the adduct of diethyl oxalate (14.61 g, 0.10 mol), ethyl benzyloxyacetate (19.42 g, 0.10 mol) and sodium hydride (4.40 g of a 60% dispersion in mineral oil, 0.11 mol) with 1-(2-hydroxyethyl)-4,5-dihydro-1H-imidazol-2-amine hydrobromide (21.0 g, 0.10 mol) as described for intermediate 1 gave 3.37 g (9% yield) of the title ester as white crystals; mp 104-106° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.32 (3H, t, J=7.1 Hz, CH3), 3.53 (2H, m, CH2), 3.83 (2H, t, J=8.9 Hz, CH2), 3.90 (2H, m, CH2), 4.19 (2H, t, J=8.9 Hz, CH2), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.11 (2H, s, OCH2), 7.35-7.40 (3H, m, aromatics), 7.51 (2H, m, aromatics). Anal. Calcd for C18H21N3O5: C, 60.16; H, 5.89, N 11.69. Found: C, 60.24; H, 5.89; N, 11.77.

Sources & evidence

ORD record
ord-21bb7846f3294260a3cc53f78ef14d73
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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