Nitrogen → HCID 131722858, compound

HRID 1596725Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([O:13][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH:3]=1.C(/C(/C)=[C:25](/[CH2:29][CH3:30])\[C:26]([NH2:28])=[O:27])C.N#N.[C:34]1(C)C=CC=C[C:35]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:56](N(CC)CC)[CH3:57]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:34]([N:28]([CH2:56][CH3:57])[C:26](/[CH:25]=[C:29](/[C:7]1[CH:2]=[CH:3][C:4]([O:13][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=1)\[CH3:30])=[O:27])[CH3:35]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of methyl (R)4-brom-2-(1-phenylethoxy)-phenylacetate (0.50 g, 1.43 mmol) and diethylcrotonamide (0.30 g, 2.1 mmol) in triethylamine (5 mL) is deoxygenated with bubbling N2 for 10 minutes in a small pressure tube. Palladium (II) acetate (16 mg, 0.07 mmol) and tris-(o-tolyl)-phosphine (44 mg, 0.14 mmol) is then added. The tube is then sealed, and the mixture heated to 100° C. for 2.5 hours. After cooling, the mixture (now dark, with precipitate present) is diluted with ethyl acetate (20 mL), and the mixture is filtered through celite, and the filtrate evaporated and chromatographed (silica, 30% ethyl acetate/hexane) to yield methyl (E)-(R)-(−)-[5-(2-diethylcarbamoyl-1-methylvinyl)-2-(1-phenylethoxy)-phenyl]-acetate as a yellow oil.

Workup

customThe tube is then sealed
temperatureAfter cooling
filtrationthe mixture is filtered through celite
customthe filtrate evaporated
customchromatographed (silica, 30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-030a85cf737a446190998da0c5b1b66e
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291530B1

Reaction notes

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