HCID 86649303, compound → HCID 68731783, compound

HRID 1523239Notes

Reaction equation

HRID 1523239 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13](=[N:21][S@@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH3:9])=[CH:4][CH:3]=1.[CH2:28]([Mg]Br)[CH:29]=[CH2:30]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C@@:13]([NH:21][S@@:22]([C:24]([CH3:26])([CH3:25])[CH3:27])=[O:23])([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[CH2:30][CH:29]=[CH2:28])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86649303HCID 86649303, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 68731783HCID 68731783, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)—N-(3-((1S)-1-(4-bromophenyl)ethylamino)-1-(4-fluorophenyl) propylidene)-2-methylpropane-2-sulfinamide (13.3 g, 29.3 mmol) in THF (300 mL) was added 1M allylmagnesium bromide (88 mL, 0.088 mol) under nitrogen at −78° C. The mixture was stirred for 2 h. The reaction was quenched with satd aq NH4Cl. The organic phase was separated and concentrated to give crude (R)—N—((R)-1-((S)-1-(4-bromophenyl)ethylamino)-3-(4-fluorophenyl)hex-5-en-3-yl)-2-methylpropane-2-sulfinamide (14 g, 100%), which was used for the next step without further purification.

Workup

  1. customThe reaction was quenched with satd aq NH4Cl
  2. customThe organic phase was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e4cb46b974ad42bd9d26a99c38024602
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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