p-Toluenesulfonic acid → (S)-cyclopentyl 2-amino-4-methylpentanoate

HRID 548253Notes

Reaction equation

HRID 548253 reaction equation
[CH3:1][C:2]1[CH:3]=CC(S(O)(=O)=O)=CC=1.C([N:14]([CH2:17][CH3:18])CC)C.[N+]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=CC=1)([O-])=O.C1C[O:34][CH2:33]C1>C(Cl)Cl>[CH:26]1([O:27][C:33](=[O:34])[C@H:17]([CH2:18][CH:2]([CH3:3])[CH3:1])[NH2:14])[CH2:25][CH2:29][CH2:30][CH2:22]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TsOH salt (7.98 g, 21.51 mmol) was dissolved in THF (40 ml) and triethylamine (6 ml, 21.5 mmol) added. 4-Nitrobenzoyl chloride (4 g, 21.5 mmol) was added portionwise with cooling, ice bath. The reaction was stirred at room temperature for 16 h before evaporation to dryness. The residue was dissolved in DCM (100 ml) and washed with saturated sodium hydrogen carbonate (3×100 ml), 1 M HCl (3×100 ml) and brine, dried (Na2SO4), and the solvent removed in vacuo. to give the required product 5.25 g (70% yield) which was used in the next step without further purification, LCMS purity 100%, m/z 349 [M++H]+

Workup

  1. temperaturewith cooling
  2. washwashed with saturated sodium hydrogen carbonate (3×100 ml), 1 M HCl (3×100 ml) and brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-378b75e1d1354a1b936fd9c18c04a16c
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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