HCID 178444813, compound → HCID 178434969, compound

HRID 14412Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16](/[N:18]=[C:19](/[NH:28][CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([NH:37][C:38](=[O:54])[CH2:39][N:40]([CH2:48][CH2:49][CH2:50][CH2:51]C=C)[C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[C:32]([Cl:55])[CH:31]=3)\[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:17])=[C:14]([CH3:56])[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]>ClCCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:24]([O:23][C:21]([NH:20][C:19]1[NH:28][CH2:29][C:30]2[CH:31]=[C:32]([Cl:55])[C:33](=[C:34]([Cl:36])[CH:35]=2)[NH:37][C:38](=[O:54])[CH2:39][N:40]([C:41]([O:42][C:43]([CH3:45])([CH3:46])[CH3:44])=[O:47])[CH2:48][CH2:49][CH2:50][CH2:51][CH:3]=[CH:2][CH2:1][O:4][C:5]2[CH:10]=[CH:9][C:8](=[CH:7][CH:6]=2)[C:11]2[C:15](=[C:14]([CH3:56])[O:13][N:12]=2)[C:16](=[O:17])[N:18]=1)=[O:22])([CH3:26])([CH3:25])[CH3:27]

Participants

Conditions

Temperature: 45 °C

Procedure

The intermediate (85 mg, 0.104 mmol) from Step 7(B) was dissolved in 27 mL of 1,2-dichloroethane, followed by the addition of Grubbs Catalyst 2nd Generation (6 mg, 0.007 mmol) with 1 mL of 1,2-dichloroethane. The resulting reaction mixture was stirred at 45° C. for 2 hrs. Solvent was evaporated in vacuo to give a crude product, which was purified by flash chromatography (8% EtOAc/DCM) to give two compounds, 8 mg of cis-8C (Rf 0.37) and 45 mg of trans-8C (Rf 0.26).

Workup

customThe resulting reaction mixture
customSolvent was evaporated in vacuo

Sources & evidence

ORD record: ord-9fef1218bf02485eb5917ae07c4a6677
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732434B2

Reaction notes

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