p-Toluenesulfonic acid → HCID 14420147, compound

HRID 977524Notes

Reaction equation

HRID 977524 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].CC1C=CC(S(O)(=O)=O)=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>N1C=CC=CC=1>[C:32]1([O:31][C:29]([NH:1][C@H:2]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:30])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 15891Phenyl chloroformateHCID 6451313Benzyl L-leucinate

Product 1

HCID 14420147HCID 14420147, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of H-Leu-OBzl.TsOH (1.01 g) in pyridine (9 ml) was added phenyl chloroformate (386 μl) at 0°-5° C. under argon atmosphere. The mixture was stirred at the same temperature for 2 h and concentrated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with 1N-hydrochloric acid, water and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel chromatography (Merck, Kieselgel 60) with ethyl acetate/hexane=1/10 for elution to give the product (828 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with 1N-hydrochloric acid, water and brine successively
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel chromatography (Merck, Kieselgel 60) with ethyl acetate/hexane=1/10 for elution

Sources & evidence

ORD record
ord-46896befd6934693b6334f8d8ba3751a
Source dataset
uspto-grants-1997_03
Patent number
US05614498

Reaction notes

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