Potassium Carbonate → 7-(2-{[3-(4-Cyanophenyl)propyl]methanesulfonylamino}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 899118Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[O:16][CH:10]([CH2:11][NH:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][N:28]([S:36]([CH3:39])(=[O:38])=[O:37])[CH2:29][CH2:30]OS(C)(=O)=O)=[CH:21][CH:20]=1)#[N:18].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[O:16][CH:14]([CH2:13][N:12]([CH2:30][CH2:29][N:28]([CH2:27][CH2:26][CH2:25][C:22]3[CH:23]=[CH:24][C:19]([C:17]#[N:18])=[CH:20][CH:21]=3)[S:36]([CH3:39])(=[O:38])=[O:37])[CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 57.5 °C

Procedure

A mixture of 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (2.35 g, 0.01 mol; see WO 01/28992), methanesulfonic acid 2-{[3-(4-cyanophenyl)propyl]methanesulfonylamino}ethyl ester (3.7 g, 0.01 mol; see Preparation A above) and anhydrous K2CO3 (2.1 g, 0.015 mol) in dry acetonitrile (70 mL) was stirred under nitrogen atmosphere at 55-60° C. for 3 days. After filtration and concentration, the crude product was purified by column chromatography (silica gel: 60-120 mesh, eluent: petroleum ether-ethyl acetate, 50:50). Yield: 3.25 g (66%).

Workup

filtrationAfter filtration and concentration
customthe crude product was purified by column chromatography (silica gel: 60-120 mesh, eluent: petroleum ether-ethyl acetate, 50:50)

Sources & evidence

ORD record: ord-21dcb69662c547549377bfcaa064083f
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354917B2

Reaction notes

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