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(1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Step lb:A solution of (lR,2S)- l-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid prepared according to the procedure described in WO2000/09558 (8.24 g; 36.3 mmol) in THF (160 mL) was treated with CDI (9.09 g; 54.4 mmol) and heated to reflux for 1 h. The resulting reaction mixture was cooled to rt and treated with Compound la (7.62 g; 50.8 mmol) followed by DBU (8.28 g; 54.4 mmol). After 16 h at rt the reaction mixture was concentrated, the residue was taken up in DCM and washed with a saturated aq solution of KHSO4 (3x). The aq phases were extracted with DCM, the organics were combined, dried over Na2S04 and concentrated in vacuo. The residue was chromatographed on silica gel (eluent: hexane/EtOAc 4: 1) to give Compound lb. LCMS (method F) Rt = 3.21 min; MS (method J): M/z = 358 [M-l ]
A solution of (1 R,25)-l -teit-butoxycarbonylamino-2-vinyl- cyclopropanecarboxylic acid prepared according to the pro-cedure described in W02000/09558 (8.24 g; 36.3 mmol) inTHF (160 mE) was treated with CDI (9.09 g; 54.4 mmol) andheated to reflux for 1 h. The resulting reaction mixture wascooled to it and treated with Compound la (7.62 g; 50.8 mmol) followed by DI3U (8.28 g; 54.4 mmol). Afier 16 hat it the reaction mixture was concentrated, the residue was taken up in DCM and washed with a saturated aq solution ofKHSO4 (3x). The aq phases were extracted with DCM, theorganics were combined, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silicagel (eluent: hexane/EtOAc 4:1) to give Compound lb. LCMS (method F) Rt=3.21 mm; MS (method J): MJz=358 [M?l]
Step 1b: A solution of <strong>[159622-10-3](1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid</strong> prepared according to the procedure described in (8.24 g; 36.3 mmol) in THF (160 mL) was treated with CDI (9.09 g; 54.4 mmol) and heated to reflux for 1 h. The resulting reaction mixture was cooled to rt and treated with Compound 1a (7.62 g; 50.8 mmol) followed by DBU (8.28 g; 54.4 mmol). After 16 h at rt the reaction mixture was concentrated, the residue was taken up in DCM and washed with a saturated aq solution of KHSO4 (3x). The aq phases were extracted with DCM, the organics were combined, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel (eluent: hexane/EtOAc 4:1) to give Compound 1b. LCMS (method F) Rt = 3.21 min; MS (method J): M/z = 358 [M-1]