Dimethyl 3-aminoglutaconate → Dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-(2-phenylethyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 342506Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]=[C:10]([C:15](=O)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]([O:13][CH3:14])=[O:12].[NH2:25][C:26]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][C:28]([O:30][CH3:31])=[O:29]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:25][C:26]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:32]1[C:33]([O:35][CH3:36])=[O:34]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 2-(2,6-dichlorophenylmethylidene)-3-oxo-5-phenylpentanoate(the crude product from the preceding experiment) and dimethyl 2-amino-1-propene-1,3-dicarboxylate (8.4 g, 48.5 mmol) was heated without solvent at 120° C. for 18 h. TLC showed a strong fluorescent spot at Rf=0.3 (dichloromethane/ethyl acetate: 24/1). This reaction mixture was chromatographed on 1.5 kg silica gel to yield 3.93 g of product. An additional 2 g of slightly impure product was also obtained.

Workup

customThis reaction mixture was chromatographed on 1.5 kg silica gel

Sources & evidence

ORD record: ord-da5d08ddaf914ef6b864111edabb632a
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859011

Reaction notes

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