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0 °C

To a magnetically stirred solution of N-t-butoxycarbonylglycine (3.00 g., 17.12 mmole) and iodopropargyl alcohol (3.12 g., 17.15 mmole) in anhydrous dichloromethane (40 ml.) cooled to 0° C. with an ice-bath was added 4-dimethylaminopyridine (0.21 g., 1.72 mmole) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.61 g., 18.83 mmole). After stirring at 0° C. for 1/2 hour, the reaction mixture was stored in a refrigerator at 6° C. overnight. The reaction mixture was transferred to a separatory funnel and diluted to 100 ml. with dichloromethane, then washed successively with water, 10% aqueous potassium hydrogen sulfate, water, saturated aqueous sodium bicarbonate, water and a final wash with saturated aqueous sodium chloride. The organic layer was dried with magnesium sulfate, filtered and concentrated in vacuo with a rotary evaporator to a clear colorless oil which crystallized on standing as N-t-butoxycarbonylglycine iodopropargyl ester (5.60 g., 96.4% yield). m.p.=65°-68° C. 1H-NMR (200 MHz, DMSOd6)δ=1.40 ppm, s, 9H; 3.73, d, 2H; 4.86, s, 2H; 7.28, t, 1H. IR (CDCl3) 1165, 1505, 1715, 1760, 2205, 3460 cm-1.

1. waitthe reaction mixture was stored in a refrigerator at 6° C. overnight
2. customThe reaction mixture was transferred to a separatory funnel
3. additiondiluted to 100 ml
4. washwith dichloromethane, then washed successively with water, 10% aqueous potassium hydrogen sulfate, water, saturated aqueous sodium bicarbonate, water
5. washa final wash with saturated aqueous sodium chloride
6. dry with materialThe organic layer was dried with magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo with a rotary evaporator to a clear colorless oil which
9. customcrystallized