Boron trifluoride etherate → HCID 18659594, compound

HRID 1608516Notes

Reaction equation

HRID 1608516 reaction equation
[CH:1]([CH:3]([NH:8][C:9](=[O:26])[C@H:10]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:4][CH2:5][CH2:6][CH3:7])=O.[CH2:27]([SH:30])[CH2:28][SH:29].B(F)(F)F.CCOCC>C(Cl)Cl>[S:29]1[CH2:28][CH2:27][S:30][CH:1]1[CH:3]([NH:8][C:9](=[O:26])[C@H:10]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 455774117591-20-5

Product 1

HCID 18659594HCID 18659594, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of anhydrous methylene chloride was dissolved 1.0 g of N-benzyloxycarbonyl-L-leucine-(1-formyl)pentylamide obtained in the same manner as in Example 4-(b), and 300 mg of 1,2-ethanedithiol and 0.8 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 900 mg of the titled compound as a colorless crystal.

Workup

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

Sources & evidence

ORD record
ord-4b71b33aea864230a7ec5f420638efcb
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

Loading…