2,6-Lutidine → HCID 10374484, compound

HRID 1585148Notes

Reaction equation

HRID 1585148 reaction equation
CO[C:3](=O)[C@H:4]([CH3:6])O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[N:23]1[C:28](C)=C[CH:26]=[CH:25][C:24]=1C.C([N:33](CC)CC)C>C(Cl)Cl>[CH3:3][C:4]1([CH3:6])[CH2:28][NH:23][CH2:24][C@@H:25]([CH3:26])[NH:33]1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 94386methyl (S)-lactate

Product 1

HCID 10374484HCID 10374484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methyl-(S)-(-)-lactate (XXVIII, 2.53 ml) in methylene chloride (130 ml) is cooled to 0°. Triflic anhydride (4.9 ml) is added and the reaction is stirred for 10 minutes at which time 2,6-lutidine (3.55 ml) is added. After an additional ten minutes of stirring at 0°, a mixture of 1-N-(triphenylmethyl)-1,2-diamino-2-methylpropane (XXVII, Step I, 7 g) and triethylamine (4.2 ml) in methylene chloride (50 ml) is added. The reaction is allowed to stir for 1 hr at 0° and 4 hr at 20-25°. After a standard basic workup (methylene chloride, sodium bicarbonate, saline and magnesium sulfate) the residue is chromatographed (silica gel; hexane/ethyl acetate, 4/1), to provide the desired compound, mp 78-80°; IR (mineral oil) 2954, 2924, 2853, 1734, 1457, 1451, 1197 and 709 cm-1 ; NMR (CDCl3) 7.50, 7.24-7.29, 7.17, 3.60, 1.71-2.93, 1.92-2.05, 1.13, 1.08 and, 1.00 δ; MS (m/e) 243, 165, 144 and 84.

Workup

  1. temperatureis cooled to 0°
  2. additionis added
  3. additionis added
  4. stirringto stir for 1 hr at 0° and 4 hr at 20-25°
  5. customAfter a standard basic workup (methylene chloride, sodium bicarbonate, saline and magnesium sulfate) the residue is chromatographed (silica gel; hexane/ethyl acetate, 4/1)

Sources & evidence

ORD record
ord-1ff12dc4e53540b7b6f53c47b50d5e07
Source dataset
uspto-grants-1999_08
Patent number
US05935970

Reaction notes

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