HCID 69463152, compound → HCID 69461682, compound

HRID 1070906Notes

Reaction equation

[CH2:1]([O:6][C:7]([C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14](=[O:34])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@@H:22]1[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH:32]=C)=[O:27])=[O:20])=[O:8])[CH2:2][CH2:3][CH:4]=C>ClCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[N:10]12[CH2:11][CH2:12][CH2:13][C@@H:9]1[C:7](=[O:8])[O:6][CH2:1][CH2:2][CH2:3][CH:4]=[CH:32][CH2:31][CH2:30][CH2:29][O:28][C:26](=[O:27])[C@@H:22]1[N:21]([CH2:25][CH2:24][CH2:23]1)[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:34]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.20 g (2.5 mmol) (R)-1-[6-[(R)-2-pent-4-enyloxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid pent-4-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 430 mg (38%) (12R,25R)-14,23-dioxa-1,8-diaza-tricyclo[23.3.0.0 8,12]octacos-18-ene-2,7,13,24-tetraone as an oil, MS m/e (%): 449 (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-0b2a6d404e964c5a974a94d46cf970bd
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903129B2

Reaction notes

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