HCID 69463158, compound → HCID 69462252, compound

HRID 1070904Notes

Reaction equation

[CH2:1]([O:4][C:5]([C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@@H:20]1[C:24]([O:26][CH2:27][CH:28]=C)=[O:25])=[O:18])=[O:6])[CH:2]=C>ClCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[N:8]12[CH2:9][CH2:10][CH2:11][C@@H:7]1[C:5](=[O:6])[O:4][CH2:1][CH:2]=[CH:28][CH2:27][O:26][C:24](=[O:25])[C@@H:20]1[N:19]([CH2:23][CH2:22][CH2:21]1)[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:30]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 420 mg (1 mmol) (R)-1-{6[-(R)-2-alloxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid allyl 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 110 mg (28%) (12R,21R)-14,19-dioxa-1,8-diaza-tricyclo[19.3.0.0 8,12]tetracos-16-ene-2,7,13,20-tetraone as light yellow oil, MS m/e (%): 393 (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-34f46aef159d4d5aaeeb035ed6ab00b8
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903129B2

Reaction notes

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