N-Succinimidyl 3-(Diphenylphosphino)propionate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of azide 2i (74 mg, 0.459 mmol) in anhydrous toluene (1.5 mL) was cooled to 0° C. A solution of phosphine 1e (171 mg, 0.482 mmol) in toluene (1.0 mL) was added dropwise. The resulting solution was maintained at 0° C. for 2 h and was then allowed to warm to room temperature. The mixture was then diluted with anhydrous CH2Cl2 (5 mL) and was stirred for an additional 30 min. The solution was then placed directly on a column of silica gel and eluted with 15% EtOAc/hexanes to give diazo-compound 5i as a yellow oil (33 mg, 0.226 mmol, 49% yield). to warm to room temperature eluted with 15% EtOAc/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-azido-6-{[(benzyloxy)carbonyl]amino}hexanoate 2f (88 mg, 0.275 mmol) was dissolved in THF/H2O (2 mL/300 μL). To this solution was added phosphine 1e (102 mg, 0.288 mmol), and the resulting solution was stirred for 5 h under Ar(g). Sat. aq. NaHCO3 (2 mL) was then added, and the mixture was stirred vigorously overnight. The mixture was then diluted with sat. aq. NaCl (15 mL) and extracted with CH2Cl2 (2×15 mL). The organic layers were combined, dried over Na2SO4(s), filtered, and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 20% EtOAc/hexanes, to give the diazo-compound 5f as a yellow oil (64 mg, 0.209 mmol, 76% yield). extracted with CH2Cl2 (2×15 mL) dried over Na2SO4(s) filtered evaporated under reduced pressure The residue was purified by silica gel flash chromatography eluting with 20% EtOAc/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-azido-6-{[(benzyloxy)carbonyl]amino}hexanoate 2f (88 mg, 0.275 mmol) was dissolved in THF/H2O (2 mL/300 μL). To this solution was added phosphine 1e (102 mg, 0.288 mmol), and the resulting solution was stirred for 5 h under Ar(g). Sat. aq. NaHCO3 (2 mL) was then added, and the mixture was stirred vigorously overnight. The mixture was then diluted with sat. aq. NaCl (15 mL) and extracted with CH2Cl2 (2×15 mL). The organic layers were combined, dried over Na2SO4(s), filtered, and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 20% EtOAc/hexanes, to give the diazo-compound 5f as a yellow oil (64 mg, 0.209 mmol, 76% yield). extracted with CH2Cl2 (2×15 mL) dried over Na2SO4(s) filtered evaporated under reduced pressure The residue was purified by silica gel flash chromatography eluting with 20% EtOAc/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of azide 2i (74 mg, 0.459 mmol) in anhydrous toluene (1.5 mL) was cooled to 0° C. A solution of phosphine 1e (171 mg, 0.482 mmol) in toluene (1.0 mL) was added dropwise. The resulting solution was maintained at 0° C. for 2 h and was then allowed to warm to room temperature. The mixture was then diluted with anhydrous CH2Cl2 (5 mL) and was stirred for an additional 30 min. The solution was then placed directly on a column of silica gel and eluted with 15% EtOAc/hexanes to give diazo-compound 5i as a yellow oil (33 mg, 0.226 mmol, 49% yield). to warm to room temperature eluted with 15% EtOAc/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-azido-6-{[(benzyloxy)carbonyl]amino}hexanoate 2f (88 mg, 0.275 mmol) was dissolved in THF/H2O (2 mL/300 μL). To this solution was added phosphine 1e (102 mg, 0.288 mmol), and the resulting solution was stirred for 5 h under Ar(g). Sat. aq. NaHCO3 (2 mL) was then added, and the mixture was stirred vigorously overnight. The mixture was then diluted with sat. aq. NaCl (15 mL) and extracted with CH2Cl2 (2×15 mL). The organic layers were combined, dried over Na2SO4(s), filtered, and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 20% EtOAc/hexanes, to give the diazo-compound 5f as a yellow oil (64 mg, 0.209 mmol, 76% yield). extracted with CH2Cl2 (2×15 mL) dried over Na2SO4(s) filtered evaporated under reduced pressure The residue was purified by silica gel flash chromatography eluting with 20% EtOAc/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of azide 2i (74 mg, 0.459 mmol) in anhydrous toluene (1.5 mL) was cooled to 0° C. A solution of phosphine 1e (171 mg, 0.482 mmol) in toluene (1.0 mL) was added dropwise. The resulting solution was maintained at 0° C. for 2 h and was then allowed to warm to room temperature. The mixture was then diluted with anhydrous CH2Cl2 (5 mL) and was stirred for an additional 30 min. The solution was then placed directly on a column of silica gel and eluted with 15% EtOAc/hexanes to give diazo-compound 5i as a yellow oil (33 mg, 0.226 mmol, 49% yield). to warm to room temperature eluted with 15% EtOAc/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-azido-6-{[(benzyloxy)carbonyl]amino}hexanoate 2f (88 mg, 0.275 mmol) was dissolved in THF/H2O (2 mL/300 μL). To this solution was added phosphine 1e (102 mg, 0.288 mmol), and the resulting solution was stirred for 5 h under Ar(g). Sat. aq. NaHCO3 (2 mL) was then added, and the mixture was stirred vigorously overnight. The mixture was then diluted with sat. aq. NaCl (15 mL) and extracted with CH2Cl2 (2×15 mL). The organic layers were combined, dried over Na2SO4(s), filtered, and evaporated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 20% EtOAc/hexanes, to give the diazo-compound 5f as a yellow oil (64 mg, 0.209 mmol, 76% yield). extracted with CH2Cl2 (2×15 mL) dried over Na2SO4(s) filtered evaporated under reduced pressure The residue was purified by silica gel flash chromatography eluting with 20% EtOAc/hexanes