Diethyl Oxalate → HCID 57565039, compound

HRID 1726888Notes

Reaction equation

HRID 1726888 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.[CH:28]([N:31]1[CH2:35][CH2:34][N:33]=[C:32]1[NH2:36])([CH3:30])[CH3:29]>>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[N:33]2[CH2:34][CH2:35][N:31]([CH:28]([CH3:30])[CH3:29])[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 69026805HCID 69026805, compound

Product 1

HCID 57565039HCID 57565039, compoundYield 38.2%

Procedure

Reaction of the adduct of diethyl oxalate (7.26 g, 49.7 mmol), ethyl benzyloxyacetate (9.65 g, 49.7 mmol) and sodium hydride (2.19 g of a 60% dispersion in mineral oil, 54.7 mmol) with 1-isopropyl-4,5-dihydro-1H-imidazol-2-amine hydrobromide (10.33 g, 49.7 mmol) as described for intermediate 1 gave 6.79 g (38% yield) of the title ester as white crystals; mp 131-132° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.22 (6H, d, J=6.8 Hz, 2×CH3), 1.31 (3H, t, J=7.1 Hz, CH3), 3.66 (2H, t, J=9 Hz, CH2), 4.13 (2H, t, J=9 Hz, CH2), 4.31 (2H, q, J=7.1 Hz, OCH2), 4.40 (1H, m, CH), 5.08 (2H, s, OCH2), 7.3-7.39 (3H, m, aromatics), 7.49 (2H, m, aromatics). Anal. Calcd for C19H23N3O4: C, 63.85; H, 6.48, N 11.75. Found: C, 63.57; H, 6.76; N, 11.98.

Sources & evidence

ORD record
ord-97a1f20cb2ab40b7b825c2efd640e44f
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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