Tributylstannane → HCID 86701269, compound

HRID 2276070Notes

Reaction equation

HRID 2276070 reaction equation
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17]I)[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH3:17])[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86701268HCID 86701268, compound

Product 1

HCID 86701269HCID 86701269, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-8-(2-iodoethyl)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (30 mg, 0.057 mmol) in benzene (1.5 mL) was added Bu3SnH (27 mg, 0.091 mmol) and AIBN (1 mg) at room temperature (about 22° C.), and the reaction solution was heated to reflux. After 1 h, the solution was cooled to room temperature. The solvent was removed under vacuum and the residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (20 mg, 88%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.44-5.19 (m, 2H), 5.03 (dd, J=13.0, 6.9 Hz, 1H), 4.91-4.73 (m, 2H), 3.70-3.52 (m, 1H), 2.68-2.52 (m, 1H), 2.45 (ddd, J=19.2, 12.0, 6.2 Hz, 1H), 1.71-1.56 (m, 2H), 1.45 (s, J=9.2 Hz, 9H), 1.26 (d, J=6.2 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H), 0.86 (t, J=7.4 Hz, 3H); ESIMS m/z 424 ([M+Na]+).

Workup

  1. temperaturethe reaction solution was heated to reflux
  2. customThe solvent was removed under vacuum
  3. customthe residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-d5604fd9b71e4a989010e6a97a9bfa90
Source dataset
uspto-grants-2015_09
Patent number
US09131690B2

Reaction notes

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