Sodium Bicarbonate → Methyl 6-{[(benzyloxy)carbonyl]amino}-2-diazohexanoate

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Reaction Steps

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).

Provenance & Evidence