HCID 178446411, compound → HCID 178435146, compound

HRID 14409

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:53])[CH2:39][N:40]([CH2:48][CH2:49][CH2:50][CH:51]=[CH2:52])[C:41](=[O:47])[O:42]C(C)(C)C)=[C:32]([Cl:54])[CH:31]=3)\[NH:20][C:21]([O:23]C(C)(C)C)=[O:22])=[O:17])=[C:14]([CH3:55])[S:13][N:12]=2)=[CH:7][CH:6]=1)C=C>ClCCCl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[C:8]([O:23][C:21]([NH:20][C:19]1[NH:28][CH2:29][C:30]2[CH:35]=[C:34]([Cl:36])[C:33](=[C:32]([Cl:54])[CH:31]=2)[NH:37][C:38](=[O:53])[CH2:39][N:40]([C:41]([O:42][C:30]([CH3:35])([CH3:31])[CH3:29])=[O:47])[CH2:48][CH2:49][CH2:50][CH:51]=[CH:52][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]([CH3:55])[S:13][N:12]=2)[C:16](=[O:17])[N:18]=1)=[O:22])([CH3:11])([CH3:9])[CH3:7]

Participants

Conditions

Temperature: 70 °C

Procedure

The intermediate (114 mg, 0.140 mmol) from Step 4(B) was dissolved in 45 mL of 1,2-dichloroethane, followed by the addition of Grubbs Catalyst 1st Generation (22 mg, 0.020 mmol) with 1 mL of 1,2-dichloroethane. The resulted reaction mixture was stirred at 70° C. for 6 hrs. (additional 14 mg of Grubbs Catalyst was added 2 hrs. after the initial addition) Solvent was evaporated in vacuo to give a crude product, which was purified by flash chromatography (10% EtOAc/DCM, Rf 0.19) to give 75 mg (68%, theoretical yield 110 mg) of the product, which is a mixture of cis and trans isomers. LCMS (method B) RT 3.78 min., MH+787.8.

Workup

customThe resulted reaction mixture
additionafter the initial addition) Solvent
customwas evaporated in vacuo

Sources & evidence

ORD record: ord-d76a862a56524df588a1981e5e8506c5
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732434B2

Linked notes

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