HCID 67171740, compound → HCID 72347756, compound

HRID 552891Notes

Reaction equation

[CH2:1]([C:4]1[CH:5]=[C:6]([CH:37]=[CH:38][CH:39]=1)[CH2:7][C@@:8]([CH3:36])([C:17]([O:19][CH2:20][C:21]1[CH:26]=[C:25]([N:27]([CH3:32])[S:28]([CH3:31])(=[O:30])=[O:29])[N:24]=[C:23]([CH2:33][CH:34]=C)[CH:22]=1)=[O:18])[NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:2]=C>ClCCCl>[CH3:36][C:8]1([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:7][C:6]2[CH:5]=[C:4]([CH:1]=[CH:2][CH:37]=2)[CH2:39][CH:38]=[CH:34][CH2:33][C:23]2=[CH:22][C:21](=[CH:26][C:25]([N:27]([CH3:32])[S:28]([CH3:31])(=[O:29])=[O:30])=[N:24]2)[CH2:20][O:19][C:17]1=[O:18]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of {2-allyl-6-[methyl(methylsulfonyl)amino]pyridine-4-yl}methyl 3-allyl-N-(tert-butoxycarbonyl)-α-methylphenylalaninate (80 mg, 0.14 mmol) in degassed DCE (2.9 mL) was added Zhan (metathesis) Catalyst I (9.2 mg, 0.014 mmol). The reaction was heated to 120° C. in a microwave for 0.5 h. Concentration and flash, chromatography (silica gel, 0-50% EtOAc/hexanes) gave tert-butyl [(3EZ)-14-methyl-8-[methyl(methylsulfonyl)amino]-13-oxo-12-oxa-7-azatricyclo[14.3.1.16,10]henicosa-1(20),3,6(21),7,9,16,18-heptaen-14-yl]carbamate. MS: 530.4 (M+1) ES+

Workup

concentrationConcentration and flash, chromatography (silica gel, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ca141053db1141a4bee2ee4d2f4ac38f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951949B2

Reaction notes

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