Stannous chloride dihydrate → HCID 58256130, compound

HRID 63249Notes

Reaction equation

[N+:1]([C:4]1[CH:26]=[C:25]([C:27](=[O:35])[NH:28][CH2:29][CH:30]2[CH2:34][CH2:33][CH2:32][O:31]2)[CH:24]=[CH:23][C:5]=1[CH2:6][N:7]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])([O-])=O.O.O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:26]=[C:25]([C:27](=[O:35])[NH:28][CH2:29][CH:30]2[CH2:34][CH2:33][CH2:32][O:31]2)[CH:24]=[CH:23][C:5]=1[CH2:6][N:7]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:13])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-nitro-4-((tetrahydrofuran-2-yl)methylcarbamoyl)benzyl(2-(pyridin-2-yl)ethyl)carbamate, from above, (238 mg, 0.492 mmol) and SnCl2.2H2O (279 mg, 1.23 mmol) were suspended in ethanol (1.6 mL) and stirred at 50° C. for 1 hour. The reaction mixture was concentrated to dryness, re-suspended in ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4, concentrated onto silica gel and purified by flash chromatography (20 methanol:1 triethylamine:79 dichloromethane isocratic) to afford the desired intermediate, tert-butyl 2-amino-4-((tetrahydrofuran-2-yl)methylcarbamoyl)benzyl(2-(pyridin-2-yl)ethyl)carbamate (103 mg). LC/MS: Calc. C25H34N4O4 454.25 amu; Obs. [M+H]+=455.5 amu.

Workup

concentrationThe reaction mixture was concentrated to dryness
washwashed with water and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated onto silica gel
custompurified by flash chromatography (20 methanol:1 triethylamine:79 dichloromethane isocratic)

Sources & evidence

ORD record: ord-6ac9ae536e0f40fa80b5d6537323e020
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447058B2

Reaction notes

Loading…