HCID 69463709, compound → HCID 69461265, compound

HRID 1070905Notes

Reaction equation

[CH2:1]([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@@H:21]1[C:25]([O:27][CH2:28][CH2:29][CH:30]=[CH2:31])=[O:26])=[O:19])=[O:7])[CH2:2]C=C>ClCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[N:20]12[CH2:24][CH2:23][CH2:22][C@@H:21]1[C:25](=[O:26])[O:27][CH2:28][CH2:29][CH:30]=[CH:31][CH2:2][CH2:1][O:5][C:6](=[O:7])[C@@H:8]1[N:9]([CH2:10][CH2:11][CH2:12]1)[C:13](=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2=[O:19]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 410 mg (0.92 mmol) (R)-1-[6-[(R)-2-but-3-enyloxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid but-3-enyl ester and 40 mg benzylidene-bis(tricyclohexylphosphine)dichlororuthenium in 30 ml dry dichloromethane was stirred at 50° C. overnight. Removal of the solvent and chromatography on silicagel with ethylacetate/acetone with a ratio of 8/2 gave 200 mg (51%) (12R,23R)-14,21-dioxa-1,8-diaza-tricyclo[21.3.0.0 8,12]hexacos-17-ene-2,7,13,22-tetraone as an oil, MS m/e (%): 421 (M+H+, 100).

Workup

customRemoval of the solvent and chromatography on silicagel with ethylacetate/acetone with a ratio of 8/2

Sources & evidence

ORD record: ord-79fd7ce55a5244d19eb7e31f656b5b6d
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903129B2

Reaction notes

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