Tributylstannane → HCID 87106334, compound

HRID 922331Notes

Reaction equation

[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30]/[C:31](=[N:38]\[O:39][CH3:40])/[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[CH:3](SC1C=CC=CC=1)[C:4]([O:6][CH3:7])=[O:5].[CH3:41]C(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[OH:1][CH:2]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30]/[C:31](=[N:38]\[O:39][CH3:40])/[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:27][CH:28]=2)=[CH:17][CH:16]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:41])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-hydroxy-3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-2-(phenylsulfanyl)propanoate (0.05 g, 0.09 mmol) in benzene was added AIBN (catalytic amount) and tributyl tin hydride, the resulting mass was refluxed at 80° C. for 4 h. RM quenched with water extracted with ethyl acetate, Organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated to yellow oil which was further purified by Preparative TLC using 10% ethyl acetate in chloroform to get the titled compound as yellow oil (0.015 g, Yield: 37.5%) 1H NMR (300 MHz, CDCl3): δ 7.63-7.65 (m, 2H), 7.32-740 (m, 5H), 7.23-7.26 (d, 2H), 6.9-6.93 (m, 4H), 5.37-5.38 (d, 1H), 5.22 (s, 2H), 4.98 (s, 2H), 4.85-4.92 (t, 1H), 3.99 (s, 3H), 3.57 (s, 3H), 3.15-3.17 (d, 1H), 2.57-2.59 (d, 2H).

Workup

customRM quenched with water
extractionextracted with ethyl acetate, Organic layer
washwas washed with water and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated to yellow oil which
customwas further purified by Preparative TLC

Sources & evidence

ORD record: ord-4f9f011ddca44823b220682e516dd849
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278915B2

Reaction notes

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