HCID 66894437, compound → (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid methyl ester

HRID 19335Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]=[C:6]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[CH2:7][NH:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])C>C(#N)C>[CH3:17][O:16][C:14](=[O:15])[C@@H:9]([N:8]1[CH2:7][C:6]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:5][C:4]1=[O:3])[CH2:10][CH2:11][S:12][CH3:13]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 3-(2-chloro-phenoxy)-4-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-but-2-enoic acid ethyl ester (1.56 g, 3.88 mmol) in acetonitrile (4 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 140° C. for 3 h. After this time, the mixture was cooled to room temperature and concentrated in vacuo with silica gel (4 g). Purification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid methyl ester (477 mg, 24% over two steps) as a golden oil: HR-ES-MS m/z calculated for C16H18NO4ClS [M+Na]+ 378.0537, observed 378.0538.

Workup

temperatureAfter this time, the mixture was cooled to room temperature
concentrationconcentrated in vacuo with silica gel (4 g)
customPurification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-880c6359a4b2451db814b3ee7e792ba3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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