Tetrahydrofuran → HCID 86608355, compound
Reaction equation
CO[CH2:3][NH2:4].C[Mg]I.[CH3:8][C:9]([C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([C:25]3[CH:26]=[C:27]([C:31]4[N:32]=[C:33]([C:44](OCC)=[O:45])[S:34][C:35]=4[C:36]4[CH:41]=[CH:40][C:39]([S:42][CH3:43])=[CH:38][CH:37]=4)[CH:28]=[CH:29][CH:30]=3)[CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([S:11]([CH3:14])(=[O:13])=[O:12])[CH3:10].C1C[O:52][CH2:51]C1>>[CH3:51][O:52][N:4]([CH3:3])[C:44]([C:33]1[S:34][C:35]([C:36]2[CH:41]=[CH:40][C:39]([S:42][CH3:43])=[CH:38][CH:37]=2)=[C:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:23]3[CH:24]=[C:15]([C:9]([CH3:10])([S:11]([CH3:14])(=[O:12])=[O:13])[CH3:8])[CH:16]=[C:17]4[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]4)[CH:26]=2)[N:32]=1)=[O:45]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
To a solution of methoxymethylamine in THF (0.08M) at −78° C. was added methylmagnesium iodide (3M, ether, 1 eq) dropwise over 1 h. The reaction mixture was stirred at −78° C. for 10 min, a solution of ester from step 1 was added and the reaction mixture was stirred at −78° C. for 2 h. The mixture was quenched with AcOH, diluted with NH4Cl solution and EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (toluene:acetone, 80:20) to afforded the title compound.
Workup
- stirringthe reaction mixture was stirred at −78° C. for 2 h
- customThe mixture was quenched with AcOH
- additiondiluted with NH4Cl solution and EtOAc
- washThe organic extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (toluene:acetone, 80:20)
Sources & evidence
- ORD record
- ord-b3223ad7bf9e46f1b92a01aa837f00de
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482456B2
Reaction notes
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