p-Toluenesulfonic acid → HCID 16047844, compound

HRID 570092Notes

Reaction equation

HRID 570092 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([CH3:19])[N:14]1[CH2:20][C:21]([NH:23][CH:24]([CH3:28])[C:25]([OH:27])=[O:26])=[O:22].O[N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.ClCCl.O>[O:36]=[C:31]1[CH2:32][CH2:33][C:34](=[O:35])[N:30]1[O:26][C:25](=[O:27])[CH:24]([NH:23][C:21](=[O:22])[CH2:20][N:14]1[CH:15]([CH3:19])[CH2:16][CH2:17][CH2:18][CH:13]1[CH3:12])[CH3:28]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 59404488HCID 59404488, compound

Product 1

HCID 16047844HCID 16047844, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4.75 g (25 mMol) p-toluenesulphonic acid were heated under reflux for 1 h in 20 ml toluene using a water separator. After having evaporating the solvent, 6.30 g (25 mMol) 2-[2-(2,6-Dimethyl-piperidin-1-yl) acetylamino]-propanoic acid (27), 2.88 g (25 mMol) N-Hydroxysuccinimide and 5.15 g (25 mMol) N,N′-Dicyclohexylcarbodiimide were added to the residue dissolved in 100 ml dichloromethane. The reaction mixture was stirred for 16 h at room temperature. The solution was filtered and the filtrate was evaporated in vacuo to dryness. The product was recrystallised from diisopropylether.

Workup

  1. additionwere added to the residue
  2. filtrationThe solution was filtered
  3. customthe filtrate was evaporated in vacuo to dryness
  4. customThe product was recrystallised from diisopropylether

Sources & evidence

ORD record
ord-416c43870ebc4b539910d8c288581fe0
Source dataset
uspto-grants-2015_05
Patent number
US09023656B2

Reaction notes

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