(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → (R)-Methyl 3-[2-[[2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]benzoate

HRID 1944920Notes

Reaction equation

HRID 1944920 reaction equation
[NH2:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C@@H:35]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:36]Br)=[C:28]2[C:33]=1[NH:32][C:31](=[O:34])[CH:30]=[CH:29]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C@@H:35]([O:38][Si:39]([C:42]([CH3:43])([CH3:45])[CH3:44])([CH3:41])[CH3:40])[CH2:36][NH:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])=[C:28]2[C:33]=1[NH:32][C:31](=[O:34])[CH:30]=[CH:29]2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 57516949Methyl 3-(2-amino-2-methylpropyl)benzoate

Product 1

HCID 58505217(R)-Methyl 3-[2-[[2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]-2-methylpropyl]benzoateYield 49%

Conditions

Temperature
95 °C

Procedure

Methyl 3-(2-amino-2-methylpropyl)benzoate (1 g, 4.82 mmol) was added to (R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one (1.57 g, 3.22 mmol) neat. The resulting mixture was heated to 95° C. for 3 d then cooled. Chromatography (1:3, hexanes/EtOAc) afforded the title compound (970 mg, 49%) as light yellow oil. ES/MS calcd. for C36H47N2O5Si+ 615.3. Found m/z=615.3 (M+H)+.

Workup

  1. temperaturethen cooled

Sources & evidence

ORD record
ord-7dcbadfcbab943d29f17e384fa9bc7ad
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

Loading…