Ethylenediamine → (1R,5R,6S) 5-(1-ethyl-propoxy)-7-aza-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([NH2:12])[C@H:9](OS(C)(=O)=O)[C@H:8]([O:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:7]=1)=[O:5])C.C(N)CN>C(O)C>[CH2:20]([CH:19]([O:18][C@H:8]1[C@@H:9]2[C@H:10]([NH:12]2)[CH2:11][C:6]([C:4]([OH:3])=[O:5])=[CH:7]1)[CH2:22][CH3:23])[CH3:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A yellowish solution of 0.87 g (2.5 mmol) (3R,4S,5R)-5-amino-3-(1-ethyl-propoxy)-4-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester and 0.17 ml (2.5 mmol) of ethylenediamine in 4.4 ml ethanol was heated to reflux for 1 hour. The resulting suspension was evaporated in a rotary evaporator to dryness and the residue was suspended in 5 ml ethyl acetate, extracted with 2 ml aqueous 1M NaHCO3 solution, dried over Na2SO4, filtered and evaporated in a rotary evaporator at reduced pressure to dryness to yield 0.52 g (82%) of (1R,5R,6S) 5-(1-ethyl-propoxy)-7-aza-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethy as a yellow oil. IR (film): 3312, 2966, 2936, 2877, 1715, 1660, 1464, 1254, 1083, 1057, 799 cm−1; MS (EI, 7o eV)): 253 (M+), 224, 208, 182, 166, 110 m/z.
Workup
- temperatureto reflux for 1 hour
- customThe resulting suspension was evaporated in a rotary evaporator to dryness
- extractionextracted with 2 ml aqueous 1M NaHCO3 solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated in a rotary evaporator at reduced pressure to dryness
Sources & evidence
- ORD record
- ord-61c37eb2f72f41ed97cbdfa02494c235
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437171B1
Reaction notes
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