p-Toluenesulfonic acid → HCID 86637728, compound

HRID 1993803Notes

Reaction equation

[C:1]([CH2:9][C:10]([O:12]CC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]1([CH2:18][NH2:19])[CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH:15]1([CH2:18][NH:19][C:10](=[O:12])[CH2:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 150 °C

Procedure

Ethyl benzoylacetate (621 mg, 3.23 mmol) and cyclopropylmethylamine (0.34 ml, 3.92 mmol) were dissolved in 1,4-dioxane (1 ml). Para-toluenesulfonic acid (3 crystals, catalytic) was added and the mixture heated under microwave irradiation at 150° C. for 30 min. The crude mixture was poured onto a SiO2 column and purified by flash chromatography (eluted with EtOAc 10 to 35% in hexanes). The title compound was isolated as a yellow solid (309 mg, 44%). HPLC (4 minutes gradient) tR 2.04 min; MS m/z 218.0 [M+H]+.

Workup

custompurified by flash chromatography (eluted with EtOAc 10 to 35% in hexanes)

Sources & evidence

ORD record: ord-3b23dce3263947a1b28498d69553eb54
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652044B2

Reaction notes

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