p-Toluenesulfonic acid → HCID 129061122, compound

HRID 1647125Notes

Reaction equation

HRID 1647125 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:22][C@H:23]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26]>ClCCl>[NH:22]([C:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9])[C@H:23]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7679Phenylacetyl chlorideHCID 6451313Benzyl L-leucinate

Product 1

HCID 129061122HCID 129061122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylacetyl chloride (5.7 ml) was added dropwise to a mixture of TsOH.H-L-Leu-OBzl (14.15 g) and TEA (12 ml) in dichloromethane (300 ml) under ice-bath cooling. After being stirred for 10 minutes at the same temperature, the mixture was concentrated in vacuo, and the residue was dissolved in ethyl acetate (300 ml). The solution was washed with 1N HCl (100 ml), water (100 ml), 1M aqueous sodium bicarbonate (100 ml), and brine (100 ml×2), dried over magnesium sulfate and evaporated to give N-phenylacetyl-L-Leu-OBzl (14 g). This product was used in a next step without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (300 ml)
  3. washThe solution was washed with 1N HCl (100 ml), water (100 ml), 1M aqueous sodium bicarbonate (100 ml), and brine (100 ml×2)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c401c6b9dbc6467fbd6d602e818938ff
Source dataset
uspto-grants-1995_07
Patent number
US05430022

Reaction notes

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