HCID 87263096, compound → HCID 67086720, compound

HRID 2365495Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17]/[CH:18]=[N:19]/[S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])=[CH:11][CH:10]=2)[CH2:4][O:3]1.[CH:27]([Mg]Br)=[CH2:28]>C1COCC1>[CH3:1][C:2]1([CH3:26])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH:18]([NH:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH:27]=[CH2:28])=[CH:13][CH:14]=2)[CH2:4][O:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-Methyl-propane-2-sulfinic acid [4-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-but-(E)-ylidene]-amide (4.51 g, 11.8 mmol) in THF (120 ml) at 0° C. is added vinylmagnesium bromide (11.8 ml of a 1 M solution in THF, 11.8 mmol) dropwise. After addition is complete, the mixture is stirred at 0° C. for 30 minutes then quenched with sat. aq. NH4Cl solution (20 ml). This mixture is allowed to warm to room temperature and diluted with water (50 ml) and EtOAc (50 ml). The organic phase is separated, dried (MgSO4) and concentrated in vacuo. Purification by chromatography (SiO2, EtOAc/iso-hexane) affords 2-Methyl-propane-2-sulfinic acid {4-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-1-vinyl-butyl}-amide as a mixture of diastereomers as a gum; [M+H]+ 410.39

Workup

additionAfter addition
customthen quenched with sat. aq. NH4Cl solution (20 ml)
temperatureto warm to room temperature
additiondiluted with water (50 ml) and EtOAc (50 ml)
customThe organic phase is separated
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customPurification by chromatography (SiO2, EtOAc/iso-hexane)

Sources & evidence

ORD record: ord-8a8713a698b3472fbea61591e4055eb3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697687B2

Reaction notes

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