Triethylamine → ((E)-3-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-1,1-dimethylallyl)-carbamic Acid Tert-butyl Ester

HRID 660524Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([O:34][C:35](=[O:42])[NH:36][C:37]([CH3:41])([CH3:40])[CH:38]=[CH2:39])([CH3:33])([CH3:32])[CH3:31].C(N(CC)CC)C>CN(C=O)C>[C:30]([O:34][C:35](=[O:42])[NH:36][C:37]([CH3:41])([CH3:40])/[CH:38]=[CH:39]/[C:13]1[CH:12]=[CH:11][C:10]([N:16]2[CH2:17][C:18](=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:20]2(=[O:22])=[O:21])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (1.4 g, 3 mmol) in DMF (20 mL) is added (1,1-dimethylallyl)-carbamic acid tert-butyl ester (560 mg, 3 mmol), triethylamine (0.7 mL, 5 mmol) and tert-di(mu-acetato) bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (25 mg). The mixture is stirred at 80° C. for 18 h. The solvent is removed under reduced pressure and the residue is purified by flash chromatography to give the title compound

Workup

customThe solvent is removed under reduced pressure
customthe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-a722fbd296ba4a7f9de580978838d3de
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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