1,4-Dioxane → HCID 68780709, compound

HRID 2266475Notes

Reaction equation

C[O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([NH2:12])[CH:6]=1.C([O:16][C:17](=O)[CH:18]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:19](=O)[CH3:20])C.O1CCOCC1.C([O-])(=O)C.[Na+]>O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:2])=[O:13])=[C:6]2[C:7]=1[NH:12][C:19]([CH3:20])=[C:18]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)[C:17]2=[O:16]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (3-amino-4-chlorophenyl)acetic acid methyl ester (1.0 g), 2-(4-chlorobenzyl)-3-oxobutyric acid ethyl ester (1.3 g), polyphosphoric acid (5 mL) and dioxane (10 mL) was heated at 130° C. for 1.5 hours. The mixture was diluted with water and the pH of this solution adjusted to 3 by the addition of sodium acetate. The resulting precipitate was collected by filtration and purified by column chromatography on silica gel, eluting with a mixture of dichloromethane, ethyl acetate and methanol (1:0:0 to 10:1:0 to 1:1:0 to 20:0:1 and 0:0:1 by volume) to afford title compound, 0.60 g.

Workup

filtrationThe resulting precipitate was collected by filtration
custompurified by column chromatography on silica gel
washeluting with a mixture of dichloromethane, ethyl acetate and methanol (1:0:0 to 10:1:0 to 1:1:0 to 20:0:1 and 0:0:1 by volume)

Sources & evidence

ORD record: ord-77d77050a8f1424e9abb196a83739cb4
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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