Water → HCID 69203626, compound

HRID 2220662Notes

Reaction equation

[OH:1][C@H:2]([C:22]1[CH:23]=[CH:24][C:25]([O:41]COCC[Si](C)(C)C)=[C:26]([N:28](COCC[Si](C)(C)C)[S:29]([CH3:32])(=[O:31])=[O:30])[CH:27]=1)[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.O.F[B-](F)(F)F.[Li+]>C(#N)C>[OH:41][C:25]1[CH:24]=[CH:23][C:22]([C@@H:2]([OH:1])[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[CH:27][C:26]=1[NH:28][S:29]([CH3:32])(=[O:31])=[O:30]

Participants

Conditions

Temperature: 80 °C

Procedure

N-[5-{(R)-1-hydroxy-2-[2-(4′-methoxybiphenyl-4-yloxy)ethylamino]ethyl}-2-(2-trimethylsilylethoxymethoxy)-phenyl]-N-(2-trimethylsilylethoxymethyl)methanesulfonamide was dissolved in acetonitrile (0.25 mL). Water (0.05 mL) and a 1 mol/L solution of lithium tetrafluoroborate in acetonitrile (0.26 mL) were added to the solution, and the mixture was stirred at 80° C. for 3 hrs. The reaction mixture was purified by reverse phase column chromatography (Shiseido Capcell Pak MG ODS, 5 μm, 120 Å, 20×50 mm, Flow rate 30 mL/minute, linear gradient 0.1% aqueous formic acid/acetonitrile=90/10-10/90 over 5 minutes). The fraction was concentrated in vacuo to afford the title compound (0.009 g).

Workup

customThe reaction mixture was purified by reverse phase column chromatography (Shiseido Capcell Pak MG ODS, 5 μm, 120 Å, 20×50 mm, Flow rate 30 mL/minute, linear gradient 0.1% aqueous formic acid/acetonitrile=90/10-10/90 over 5 minutes)
concentrationThe fraction was concentrated in vacuo

Sources & evidence

ORD record: ord-04aef3285c4c45228543df50e168ea72
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417169B2

Reaction notes

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