Diethyl Oxalate → HCID 57565048, compound

HRID 1726900Notes

Reaction equation

HRID 1726900 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.[CH2:28]([N:35]1[CH2:39][CH2:38][N:37]=[C:36]1[NH2:40])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([N:35]1[C:36]2=[N:40][C:2]([C:1]([O:8][CH2:9][CH3:10])=[O:7])=[C:19]([O:18][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:20](=[O:22])[N:37]2[CH2:38][CH2:39]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 12491144HCID 12491144, compound

Product 1

HCID 57565048HCID 57565048, compoundYield 18.7%

Procedure

Reaction of the adduct of diethyl oxalate (7.66 g, 52.4 mmol), ethyl benzyloxyacetate (10.2 g, 52.5 mmol) and sodium hydride (2.31 g of a 60% dispersion in mineral oil, 57.9 mmol) with 1-benzyl-4,5-dihydro-1H-imidazol-2-amine hydrobromide (13.39 g, 52.5 mmol) as described for intermediate 1 gave 3.98 g (18% yield) of the title ester as white crystals; mp 93° C. (ethyl acetate-hexane).

Sources & evidence

ORD record
ord-a723c6e116a94c27b673ecb17278b68f
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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