Trifluoromethanesulfonic acid → N-[[1,2,3,4-tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-valine

HRID 1656048Notes

Reaction equation

HRID 1656048 reaction equation
[C:1]([S:5][CH2:6][C:7]1([C:17]([NH:19][C@H:20]([C:24]([O:26]CC2C=CC=CC=2)=[O:25])[CH:21]([CH3:23])[CH3:22])=[O:18])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(O)(=O)=O>CSC.O>[C:1]([S:5][CH2:6][C:7]1([C:17]([NH:19][C@H:20]([C:24]([OH:26])=[O:25])[CH:21]([CH3:22])[CH3:23])=[O:18])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 131718216N-[[1,2,3,4-Tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-valine, benzyl ester

Product 1

HCID 54083017N-[[1,2,3,4-tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-valine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1068Dimethyl SulfideSolvent

Procedure

Dissolve N-[[1,2,3,4-tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-valine, benzyl ester (256 mg, 0.547 mmol) in dimethylsulfide (3 mL) and add trifluoromethanesulfonic acid (0.2 mL). Stir at room temperature under an argon atmosphere for 6 hours. Dilute with water and extract into ethyl ether. Wash with water, then brine and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound.

Workup

  1. extractionextract into ethyl ether
  2. washWash with water
  3. dry with materialbrine and dry (MgSO4)
  4. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-03ba3e247aa64ddb8bd9aa4d5ae5611f
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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