Hydrochloric Acid → BOC-Leu-Lys(Z)

HRID 330054Notes

Reaction equation

HRID 330054 reaction equation
[NH2:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Cl.[NH:22]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:23]([C:28](O)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26]>CN(C=O)C>[NH:22]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[C@H:23]([C:28]([NH:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine

Product 1

HCID 13857776BOC-Leu-Lys(Z)Yield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 200 ml of 1.5N NEM/DMF mixture, 45.2 g (0.2 mol) of H-Lys(Z)-CHA.HCl was dissolved, and 35.3 g (0.1 mol) of BOC-Leu-SDP was added thereto at 0° to 5° C. The reaction was carried out at room temperature for 18 hours. After the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 1500 ml of AcOEt and washed with 500 ml of a cooled 5% HCl solution twice, and 500 ml of a saturated saline solution twice, followed by decoloration and drying over anhydrous magnesium sulfate and active carbon. After drying, the magnesium sulfate and active carbon were filtered and the solvent was removed by distillation under reduced pressure to yield crude BOC-Leu-Lys(Z)-CHA. This was recrystallized from a mixed solvent of AcOEt/ether/n-hexane to give 35.9 g (57.1%) of BOC-Leu-Lys(Z)-CHA.

Workup

  1. customat 0° to 5° C
  2. customAfter the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in 1500 ml of AcOEt
  5. washwashed with 500 ml of a cooled 5% HCl solution twice
  6. dry with materialdrying over anhydrous magnesium sulfate and active carbon
  7. customAfter drying
  8. filtrationthe magnesium sulfate and active carbon were filtered
  9. customthe solvent was removed by distillation under reduced pressure
  10. customto yield crude BOC-Leu-Lys(Z)-CHA
  11. customThis was recrystallized from a mixed solvent of AcOEt/ether/n-hexane

Sources & evidence

ORD record
ord-9c6fcb88b0d740738d2cc9715b994115
Source dataset
uspto-grants-1990_01
Patent number
US04894438

Reaction notes

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