Tetrahydrofuran → HCID 67885081, compound

HRID 1656372Notes

Reaction equation

C(OC([C:7]1[N:8]=[CH:9][C:10]2[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:14][CH:13]=3)=O)(C)C.[C:44]1([Li])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[O:51]1CCC[CH2:52]1>CCOCC.CCCCCC>[CH2:52]([O:51][C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:26])[CH3:27])=[CH:14][CH:13]=3)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of 230 mg of 4-methoxymethyl-9-tosyl-6-triisopropylsilyloxy-beta-carboline-3-carboxylic acid isopropyl ester in 3.5 ml of absolute tetrahydrofuran was mixed at -60° C. under argon with 0.38 ml of a 1.08 molar phenyllithium solution in ether/hexane, stirred for 1 hour at -60° C. and heated slowly to room temperature. After 16 hours of standing at room temperature, the reaction mixture was mixed with N-acetic acid/ethyl acetate, the ethyl acetate phase was washed with water and saturated sodium chloride solution, dried and concentrated by evaporation. After column chromatography on silica gel with cyclohexane/ethyl acetate 1:1 as eluant, 69 mg of title compound was obtained.

Workup

temperatureheated slowly to room temperature
waitAfter 16 hours of standing at room temperature
washthe ethyl acetate phase was washed with water and saturated sodium chloride solution
customdried
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-f7d8c8856b6c4820b6c3742130536104
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254563

Reaction notes

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