Boron trifluoride etherate → HCID 18659593, compound

HRID 1608517Notes

Reaction equation

HRID 1608517 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:31])[CH2:28][CH2:29][SH:30].B(F)(F)F.CCOCC>C(Cl)Cl>[S:30]1[CH2:29][CH2:28][CH2:27][S:31][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 80131,3-PropanedithiolHCID 455774117591-20-5

Product 1

HCID 18659593HCID 18659593, compoundYield 72.1%

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 1,3-propanedithiol 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-5e5b8aec39454ff48b3bb82a1577ad37
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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