p-Toluenesulfonic acid → HCID 54305758, compound

HRID 1415888Notes

Reaction equation

HRID 1415888 reaction equation
[CH2:1]([C:5]1([CH2:8][CH3:9])[CH2:7][NH:6]1)[CH2:2][CH2:3][CH3:4].[SH:10][C:11]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C(C)=CC=CC=1C>[CH2:1]([C:5]1([CH2:8][CH3:9])[CH:7]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]2[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:11]=2[S:10][NH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 217099702-Butyl-2-ethylaziridineHCID 22325205HCID 22325205, compound

Product 1

HCID 54305758HCID 54305758, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent2×

Procedure

The product (55.2 g) from step (i), in 2,6-lutidine (100 ml), was added to a solution of the product (118.5 g) from step (c) in 2,6-lutidine (400 ml). The reaction mixture was stirred for 1 hour and p-toluenesulfonic acid (9.0 g) was added and then refluxed with a Dean Stark trap for 17 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between 5% NaHCO3 and EtOAc. The organic layer was separated, dried and concentrated to get an oil which was chromatographed on silica gel, using hexane: EtOAc (85:15) as the eluant, to afford the title product (124.3 g) as an orange oil. 1H NMR consistent with the desired structure.

Workup

  1. temperaturerefluxed with a Dean Stark trap for 17 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between 5% NaHCO3 and EtOAc
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto get an oil which
  8. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-9fafd088a8e941fd935547eb1134437b
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

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