Reaction #40296

Reaction equation

compound

(2R,3S)-3-Benzyloxycarbonylamino-5,5-dimethyl-2-hydroxyhexane

N,N-diisopropylethylamine

→

(3S)-3-Benzyloxycarbonylamino-5,5-dimethyl-2-oxohexane

Solvents

DMSO

Conditions

Workup

1. 1
   ExtractionThe mixture is extracted four times with diethyl ether
2. 2
   WashThe combined organic phases are washed three times with a 10% citric acid solution
3. 3
   Dryingsodium chloride solution, dried over magnesium sulfate
4. 4
   Concentrationconcentrated at 20° C. on a Rotavapor
5. 5
   OtherThe crude product (30 mg, 60% of th.) is reacted further without additional purification

Procedure

Pyridine-SO3 complex (285 mg, 1.79 mmol) is added to a solution of the compound of Example 68A (50 mg, 0.18 mmol) and N,N-diisopropylethylamine (310 μl, 1.79 mmol) in 2 ml of DMSO at 10° C. with and the mixture is slowly warmed to RT. After 2 h, 50 ml of ice/water are added to the reaction mixture. The mixture is extracted four times with diethyl ether. The combined organic phases are washed three times with a 10% citric acid solution, then three times with water and twice with a satd. sodium chloride solution, dried over magnesium sulfate and concentrated at 20° C. on a Rotavapor. The crude product (30 mg, 60% of th.) is reacted further without additional purification.

Source