Trifluoromethanesulfonic acid → N-[[1,2,3,4-tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine

HRID 1656059Notes

Reaction equation

HRID 1656059 reaction equation
[C:1]([S:4][CH2:5][C:6]1([C:16]([NH:18][CH2:19][CH:20]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])[OH:21])=[O:17])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=[O:3])[CH3:2].FC(F)(F)S(O)(=O)=O>CSC.C(Cl)Cl>[C:1]([S:4][CH2:5][C:6]1([C:16]([NH:18][CH2:19][CH:20]([C:22]([OH:24])=[O:23])[OH:21])=[O:17])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 88127936N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

Product 1

HCID 19789945N-[[1,2,3,4-tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve N-[[1,2,3,4-tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester (882 mg, 2.00 mmol) in dimethylsulfide (2 mL) and add trifluoromethane sulfonic acid (0.2 mL). Stir at ambient temperature under an atmosphere of argon for 1 hour. Dilute to a volume of 50 mL with methylene chloride and extract with brine. Dry (MgSO4) and evaporate the solvent in vacuo to give the crude product. Purify the residue by column chromatography (acetic acid:ethyl acetate:hexane) to give the title compound.

Workup

  1. extractionextract with brine
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. customto give the crude product
  5. customPurify the residue by column chromatography (acetic acid:ethyl acetate:hexane)

Sources & evidence

ORD record
ord-0566721938d146c181fe5330a0027b7b
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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