2,6-Lutidine → HCID 22859446, compound

HRID 1440514Notes

Reaction equation

HRID 1440514 reaction equation
[C:1]([O:6][CH3:7])(=O)[C@@H:2]([CH3:4])O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.N1[C:28](C)=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30].C1([SH:37])C=CC=CC=1>CC#N>[CH3:7][O:6][C:1](=[S:37])[C@H:2]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:30]=1)[CH3:4]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 7969ThiophenolHCID 67749Trifluoromethanesulfonic anhydrideHCID 637514(+)-Methyl lactate

Product 1

HCID 22859446HCID 22859446, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-Methyl lactate (0.553 g, 5.31 mol) was carried through the reaction sequence of Example 5 with triflic anhydride (1.03 ml, 6.11 mmol) and 2,6-lutidine (0.74 ml, 6.38 mmol) in 10 ml of CH3CN. Thiophenol (0.73 ml, 6.91 mmol) and TEA (1.93 ml, 13.8 mmol) were added and the workup described in Example 5 followed by purification by silica gel chromatography using 25 to 1 hexane to ethyl acetate as eluent gave (S)-methyl-2-phenylthiopropionate as a clear yellow oil (0.511 g, 2.60 mmol, 49%). [α]D =-165.4° (c=1.2, MeOH). 1H NMR δ7.43 (m, 2H), 7.29 (m, 3H), 3.78 (q, 1H, J =7.12 Hz), 3.65 (s, 3H)), 1.47 (d, 3H, J=7.12 Hz); 13C NMR δ172.87, 133.15, 133.01, 128.92, 128.00, 52.11, 45.07, 17.43.

Workup

  1. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-1fbbda397aff4ddaaea558d3477a7473
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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