HCID 86691106, compound → HCID 86691105, compound

Participants

Reaction Steps

(3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-({1-(2-azido-ethyl}-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester (46) and Lindlar catalyst in ethanol was added. The flask was charged with hydrogen gas (1 atm) at room temperature. The resulting suspension was vigorously stirred for 24 hours. The reaction mixture was diluted with dichloro methane and the combined organic layers were filtered through a Celite pad. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the (3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-({1-(2-amino-ethyl}-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester as a pale yellow liquid, which was used without further purification in the next step. (3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-({1-(2-amino-ethyl}-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester was coupled with Fmoc-PEG-acid (16 atoms) in the presence of EDC, HOBT plus DIPEA in dichloro methane. The solution was stirred over a period of 18 hours the room temperature. The crude product was purified by a silica column chromatography using a 8:2 mixture of dichloro methane and hexane. The combined fractions were evaporated and dried over Na2SO4 and the combined organic phases were evaporated on a rotary evaporator to obtain as (3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-({1-(2-Fmoc-Peg-amide-ethyl}-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester (47).

Provenance & Evidence