Reaktion #53985

Reaktionsgleichung

sodium bicarbonate

(1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[-(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate

(1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate

hydrochloric acid

→

(1S,2S)-2-{[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate

Ausbeute 75.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×75 ml)
2. 2
   Waschenthe combined organics were washed with saturated sodium chloride
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was chromatographed (flash column, silica gel, 45% ethyl acetate in hexane)

Vorschrift

To a solution of (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[-(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate (1.06 g, 1.79 mmol, obtained from Reference Example 47) in anhydrous tetrahydrofuran was added 0.5 N hydrochloric acid (4.3 ml). The resulting solution was stirred at room temperature for 5 hours. The reaction mixture was brought to pH 9 with aqueous sodium bicarbonate, extracted with ethyl acetate (3×75 ml), the combined organics were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 45% ethyl acetate in hexane) to provide (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate (694 mg, 75%) as a white solid.

Quelle