HCID 87263096, compound → HCID 67086720, compound

HRID 2281569Notes

Reaction equation

HRID 2281569 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

4

Reactant 2

HCID 87263096HCID 87263096, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 67086720HCID 67086720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

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

Sources & evidence

ORD record
ord-6faae6d85a4542a0b0fa123ba1927a30
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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