Dimethylformamide → Isohexane ethyl acetate

HRID 658338Notes

Reaction equation

[CH:1]([O:4][C:5](=[S:19])[NH:6][C:7]1[CH:12]=[C:11](F)[CH:10]=[C:9]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=1)([CH3:3])[CH3:2].[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].CN(C)[CH:27]=[O:28]>O1CCCC1>[C:15]([O:14][C:9]1[CH:10]=[C:11]([CH:27]=[O:28])[C:12]2[S:19][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[N:6][C:7]=2[CH:8]=1)([CH3:18])([CH3:17])[CH3:16].[C:9]([O:14][CH2:15][CH3:18])(=[O:28])[CH3:8].[CH3:1][CH2:2][CH2:21][CH:20]([CH3:23])[CH3:22]

Participants

Conditions

Temperature: -78 °C

Procedure

(3-tert-Butoxy-5-fluoro-phenyl)-thiocarbamic acid O-isopropyl ester (2.2 g) is dissolved in dry tetrahydrofuran (20 ml) The reaction mixture is cooled to −78° C. and tert-butyl lithium (15.2 ml, of 1.5 M solution) is added over 20 minutes. The reaction mixture is then warmed to −10° C. for 75 minutes. The reaction mixture is then re-cooled to −78° C., N,N-dimethylformamide (1.5 g) is added and the reaction mixture is slowly warmed to room temperature then stirred at −10° C. for 1 hour. The reaction mixture is quenched with HCl(aq) (5 ml, of a 2 M solution), the organics are separated between ethyl acetate/water and removed in vacuo. The title compound is obtained by flash column chromatography (silica, eluent ethyl acetate/iso-hexane 1:9). MS (ES+) m/e 294 (MH+) LCT50865

Workup

temperatureThe reaction mixture is then warmed to −10° C. for 75 minutes
temperatureThe reaction mixture is then re-cooled to −78° C.
temperaturethe reaction mixture is slowly warmed to room temperature
customThe reaction mixture is quenched with HCl(aq) (5 ml
customof a 2 M solution), the organics are separated between ethyl acetate/water
customremoved in vacuo

Sources & evidence

ORD record: ord-42474faee7a84efb8558c336a311d17b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076489B2

Reaction notes

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