(N-Acetyl)-(4R)-benzyl-2-oxazolidinone → 4-Benzyl-3-[3-(4-benzyloxy-3-cyclopentyloxyphenyl)-4-nitrobutyryl]-oxazolidin-2-one

HRID 1727140Notes

Reaction equation

[C:1]([N:4]1[CH:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][O:6][C:5]1=[O:16])(=[O:3])[CH3:2].C(NC(C)C)(C)C.[Li].[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]=[CH:40][N+:41]([O-:43])=[O:42])=[CH:35][C:34]=1[O:44][CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:9]([CH:8]1[CH2:7][O:6][C:5](=[O:16])[N:4]1[C:1](=[O:3])[CH2:2][CH:39]([C:36]1[CH:37]=[CH:38][C:33]([O:32][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:34]([O:44][CH:45]2[CH2:49][CH2:48][CH2:47][CH2:46]2)[CH:35]=1)[CH2:40][N+:41]([O-:43])=[O:42])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 3-acetyl-4-benzyl-oxazolidin-2-one (2.1 g, 9.4 mmol) in THF (40 mL) was stirred under N2 at −78° C. Lithium diisopropyl amine (5.2 mL, 10.3 mmol, 2.0 M in heptane/THF/ethylbenzene) was then added dropwise. The mixture was stired for 20 min. 1-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzene (3.2 g, 9.4 mmol) dissolved in 20 mL THF was cannulated over and the mixture was stirred for 2 h at −78° C. After quenching the reaction sat. NH4Cl, the mixture was warmed to r.t., extracted with CH3Cl, washed with water and brine, dried and concentrated. Filtration of the solids with 1:1 hexane/EtOAc, afforded 4 g of white solids. Yield: 75%.

Workup

stirringwas stirred for 2 h at −78° C
customAfter quenching the reaction sat. NH4Cl
temperaturethe mixture was warmed to r.t.
extractionextracted with CH3Cl
washwashed with water and brine
customdried
concentrationconcentrated
filtrationFiltration of the solids with 1:1 hexane/EtOAc

Sources & evidence

ORD record: ord-26bf68a7564540a582fcf64ce89cb791
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495016B2

Reaction notes

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