Homoallyl bromide → HCID 86691465, compound

HRID 405691Notes

Reaction equation

[CH:1]([C@H:4]1[C:20](=[O:21])[O:19][C@H:18]([CH:22]=[CH2:23])[CH2:17][C:16](=[O:24])[NH:15][CH2:14][C:13]2=[N:25][C:10](=[CH:11][S:12]2)[C:9](=[O:26])[NH:8][C:7]([CH3:28])([CH3:27])[C:6](=[O:29])[NH:5]1)([CH3:3])[CH3:2].[Br:30][CH2:31][CH2:32]C=C>ClCCCl>[Br:30][CH2:31][CH2:32]/[CH:23]=[CH:22]/[C@@H:18]1[CH2:17][C:16](=[O:24])[NH:15][CH2:14][C:13]2=[N:25][C:10](=[CH:11][S:12]2)[C:9](=[O:26])[NH:8][C:7]([CH3:27])([CH3:28])[C:6](=[O:29])[NH:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C:20](=[O:21])[O:19]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a mixture of (7S,10S)-7-isopropyl-4,4-dimethyl-10-vinyl-9-oxa-16-thia-3,6,13,18-tetraazabicyclo[13.2.1]octadeca-1(17),15(18)-diene-2,5,8,12-tetraone (20 mg, 0.047 mmole) in 2 mL 1,2-dichloroethane was added 4-bromo-1-butene (25.6 mg, 0.19 mmole) and Zhan-1 catalyst (3.2 mg, 0.0047 mmole). The mixture was briefly degassed and then heated in a sealed tube at 85° C. overnight. The crude product was concentrated and passed through a silica gel plug to get a mixture of the desired product and recovered starting material (2:1 ratio). It was further purified by reversed phase chromatography, eluted with 0-80% water/CH3CN to get the desired product (8 mg, 32% yield).

Workup

customThe mixture was briefly degassed
concentrationThe crude product was concentrated
customto get

Sources & evidence

ORD record: ord-99efdbfb0184437ebeb79a2bb531ec6b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754050B2

Reaction notes

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