Boron trifluoride etherate → HCID 15228359, compound

HRID 1608522Notes

Reaction equation

HRID 1608522 reaction equation
[CH:1]([CH:3]([NH:8][C:9](=[O:19])[C@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:11][C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][CH2:6][CH3:7])=O.[CH2:20]([SH:23])[CH2:21][SH:22].B(F)(F)F.CCOCC>C(Cl)Cl>[S:22]1[CH2:21][CH2:20][S:23][CH:1]1[CH:3]([NH:8][C:9](=[O:19])[C@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:11][C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 15228355HCID 15228355, compound

Product 1

HCID 15228359HCID 15228359, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of methylene chloride was dissolved 1.8 g of N-acetyl-L-leucine-(1-formyl)pentylamide obtained in the same manner as in Example 16-(c), and 700 mg of 1,2-ethanedithiol and 1.5 ml of boron trifluoride ethyl etherate were added thereto. The mixture was allowed to react at room temperature for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel to obtain 1.7 g of the titled compound as a colorless crystal.

Workup

  1. additionwere added
  2. customto react at room temperature for 12 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-3892983d4c4847b6b6ab2e0fdade112b
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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