2,6-Lutidine → HCID 54204795, compound

HRID 1440513Notes

Reaction equation

HRID 1440513 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]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1C.C([SH:37])CCCCC>CC#N>[CH3:7][O:6][C:1](=[S:37])[C@@H:2]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:4]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 81061-HexanethiolHCID 67749Trifluoromethanesulfonic anhydrideHCID 94386methyl (S)-lactate

Product 1

HCID 54204795HCID 54204795, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-Methyl lactate (0.571 g, 5.27 mmol) was carried through the reaction sequence of Example 5 with triflic anhydride (1.02 ml, 6.05 mmol) and 2,6-lutidine (0.71 ml, 6.05 mmol) in 11 ml of CH3CN. Hexanethiol (1.02 ml, 6.84 mmol) and TEA (1.91 ml, 13.7 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 (R)-methyl-2-hexylthiopropionate as a clear yellow oil (0.933 g, 4.56 mmol, 86%). [α]D =+130.0° (c=1, MeOH). Anal. Calcd. for C10H20O2S: C, 58.78; H, 9.87: Found: D, 58.76; H, 9.99%.

Workup

  1. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-69b8e37e4e8a4b029ade27343afda00d
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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