Fmoc-Gly-OH → ({2-[2-(N-(tert-butoxycarbonyl)-N-methylamino)ethyl]phenylcarbamoyl}methyl)carbamic acid ((9-fluorenyl)methyl) ester

Temperature

0 °C

2-(((9-Fluorenyl)methoxycarbonyl)amino)acetic acid (2.49 g, 2.79 mmol) was suspended in dichloromethane (40 ml). The suspension was cooled to 0° C. N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (802 mg, 4.19 mmol) was added. The reaction mixture was stirred for 30 min at 0° C. A solution of N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (698 mg, 2.79 mmol) in dichloromethane (15 ml) was added. The reaction mixture was stirred for 16 h, while it was warming up to room temperature. It was diluted with dichloromethane (100 ml) and washed with brine (100 ml). The aqueous solution was extracted with dichloromethane (2×30 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using ethyl acetate/heptane (1:1) as eluent, to give 1.412 g of ({2-[2-(N-(tert-butoxycarbonyl)-N-methylamino)ethyl]phenylcarbamoyl}methyl)carbamic acid ((9-fluorenyl)methyl) ester.

1. stirringThe reaction mixture was stirred for 16 h, while it
2. temperaturewas warming up to room temperature
3. washwashed with brine (100 ml)
4. extractionThe aqueous solution was extracted with dichloromethane (2×30 ml)
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. customThe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography on silica (80 g)

ORD record

ord-12be51cfe44d4db1b5c0573c91873f78

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127354