Sodium Carbonate → N1-((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine

HRID 1523258Notes

Reaction equation

HRID 1523258 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20]([NH:31][S@@](C(C)(C)C)=O)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22]([CH3:24])=[CH2:23])C(=O)OC(C)(C)C)[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][CH2:18][CH2:19][C:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([NH2:31])[CH2:21][C:22]([CH3:24])=[CH2:23])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 59627246tert-butyl (S)-1-(4-bromophenyl)ethyl(3-((R)-1,1-dimethylethylsulfinamido)-5-methyl-3-phenylhex-5-enyl)carbamate

Product 1

HCID 59627223N1-((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamineYield 70%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl (S)-1-(4-bromophenyl)ethyl(3-((R)-1,1-dimethylethylsulfinamido)-5-methyl-3-phenylhex-5-enyl)carbamate (6.5 g, 0.011 mol) in HCl/dioxane (70 mL) was stirred for 1 hour at 0° C. The mixture was concentrated to give the residue, which was treated with satd aq Na2CO3. The resulting mixture was extracted with EtOAc, and the combined organic layer was concentrated to afford crude N1—((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine (2.97 g, 70%), which was used for the next step without purification.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the residue, which
  3. extractionThe resulting mixture was extracted with EtOAc
  4. concentrationthe combined organic layer was concentrated

Sources & evidence

ORD record
ord-14d9d37947034348b849e115f3731500
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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