4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 8-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848532Notes

Reaction equation

[O:1]=[C:2]1[O:6][CH2:5][C:4]([N:7]2[CH2:11][CH2:10][C:9]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:8]2=[O:17])=[CH:3]1.[CH3:18][C:19]1[C:27]2[CH2:26][O:25][C:24](=[O:28])[C:23]=2[CH:22]=[CH:21][C:20]=1[C@@H:29]1[CH2:31][O:30]1>C(O)C>[OH:30][C@H:29]([C:20]1[CH:21]=[CH:22][C:23]2[C:24](=[O:28])[O:25][CH2:26][C:27]=2[C:19]=1[CH3:18])[CH2:31][N:14]1[CH2:13][CH2:12][C:9]2([C:8](=[O:17])[N:7]([C:4]3[CH2:5][O:6][C:2](=[O:1])[CH:3]=3)[CH2:11][CH2:10]2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 145 °C

Procedure

2-(5-Oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-16, 200 mg, 0.846 mmol) was combined with 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (I-4B) (177 mg, 0.931 mmol) in ethanol (5 mL) and heated in a microwave apparatus at 145° C. for 3 hours. The solvent was removed and the residue was purified by preparative TLC, eluting with 25% methanol/EtOAc to afford the title compound. LC-MS (IE, m/z): 427 (M+1)+.

Workup

customThe solvent was removed
customthe residue was purified by preparative TLC
washeluting with 25% methanol/EtOAc

Sources & evidence

ORD record: ord-3635a8ec546d44c5b748a4a3681b032d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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