Anisole → N-(2-acetylthiomethyl-4-phenylbutanoyl)-(L)-leucine

HRID 1780025Notes

Reaction equation

HRID 1780025 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:7]([NH:9][C@H:10]([C:15]([O:17]C(C)(C)C)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[C:1]([S:4][CH2:5][CH:6]([CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 54107687N-(2-Acetylthiomethyl-4-phenylbutanoyl)-(L)-Leucine t-butyl ester

Product 1

HCID 53805712N-(2-acetylthiomethyl-4-phenylbutanoyl)-(L)-leucineYield 73%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The higher RfTLC fraction product of N-(2-acetylthiomethyl-4-phenylbutanoyl)-(L)-leucine, t-butyl ester (1.90 g, 4.5 mmole) was dissolved in 5 mL of trifluoroacetic acid (TFA) and 420 mg anisole at 0° C. for 18 h. No starting material was observed by TLC. The TFA was azeotroped off under reduced pressure with benzene. The product was suspended in hexane and filtered to remove the anisole. Recovered 1.2 g of N-(2-acetylthiomethyl-4-phenylbutanoyl)-(L)-leucine (73% yield).

Workup

  1. customThe TFA was azeotroped off under reduced pressure with benzene
  2. filtrationfiltered
  3. customto remove the anisole

Sources & evidence

ORD record
ord-d9ff745f4aa04020818caf29632c0892
Source dataset
uspto-grants-1997_05
Patent number
US05629343

Reaction notes

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