methyl 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valyl-(4R)-4-[(7-methoxy-3-vinylquinoxalin-2-yl)oxy]-L-prolinate → Methyl (33R,35S,91R,92R,5S,E)-5-(tert-butyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphan-13-ene-35-carboxylate

HRID 659829Notes

Reaction equation

[CH3:1][C:2]([CH3:43])([CH3:42])[C@@H:3]([C:16]([N:18]1[CH2:26][C@H:25]([O:27][C:28]2[C:37]([CH:38]=C)=[N:36][C:35]3[C:30](=[CH:31][C:32]([O:40][CH3:41])=[CH:33][CH:34]=3)[N:29]=2)[CH2:24][C@H:19]1[C:20]([O:22][CH3:23])=[O:21])=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=C)=[O:6]>ClCCCl>[C:2]([C@H:3]1[C:16](=[O:17])[N:18]2[CH2:26][C@@H:25]([CH2:24][C@H:19]2[C:20]([O:22][CH3:23])=[O:21])[O:27][C:28]2=[N:29][C:30]3[CH:31]=[C:32]([O:40][CH3:41])[CH:33]=[CH:34][C:35]=3[N:36]=[C:37]2[CH:38]=[CH:14][CH2:13][CH2:12][CH2:11][C@@H:9]2[CH2:10][C@H:8]2[O:7][C:5](=[O:6])[NH:4]1)([CH3:43])([CH3:1])[CH3:42]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution (0.02 M) of methyl 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valyl-(4R)-4-[(7-methoxy-3-vinylquinoxalin-2-yl)oxy]-L-prolinate in DCE was heated to 80° C. then treated with Zhan 1 catalyst (0.15 eq). The resulting mixture was stirred at 80° C. for 1 h, then cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (20-50% EtOAc/petroleum ether) to give the title compound (25% for 2 steps) as a foam. MS (ES+) m/z 567 (M+H)+

Workup

temperaturecooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (20-50% EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-1ec90fc3874649bb844846a1751b0641
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080654B2

Reaction notes

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