Potassium Carbonate → 3-((R)-4-Cyclohexyl-2-oxo-oxazolidin-3-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

HRID 579189Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]#[C:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1Br)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH:23]1([C@@H:29]2[CH2:33][O:32][C:31](=[O:34])[NH:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>[Cu]I.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]#[C:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]=1[N:30]1[C@H:29]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:33][O:32][C:31]1=[O:34])=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

A heavy wall flask was charged with trans-cyclohexane diamine (18.9 mg, 0.17 mmol, 0.5 equiv), 3-bromo-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (100 mg, 0.332 mmol, 1.0 equiv), K2CO3 (92 mg, 0.664 mmol, 2.0 equiv), CuI (31.6 mg, 0.166 mmol, 0.5 equiv), (R)-4-cyclohexyl-oxazolidin-2-one (56.2 mg, 0.332 mmol, 1.0 equiv) and 1,4-dioxane (0.5 mL). The mixture was flushed with N2 and stirred at 110° C. for 18 hours, after which the mixture was filtered through celite and the filtrate was concentrated under vacuum. The residue was purified by silica gel, EtOAc/heptane 30% to give product 54 mg (yield 42%).

Workup

customThe mixture was flushed with N2
filtrationafter which the mixture was filtered through celite
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified by silica gel, EtOAc/heptane 30%

Sources & evidence

ORD record: ord-d20d6d9c2889493abdea14ef20ed7b77
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040690B2

Reaction notes

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