反応 #681370

反応方程式

glycine tert-butyl ester hydrogen chloride salt

Fmoc-Gly-OH

DIPEA

HATU

→

tert-butyl 2-(2-aminoacetamido)acetate

溶媒

ethyl acetate

dichloromethane

反応条件

後処理

1. 1
   洗浄was washed with water (3×) and brine (1×)
2. 2
   乾燥The organic phase was dried over MgSO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The resulting residue was purified via radial chromatography on a 2 mm plate
6. 6
   洗浄eluting with 5% methanol/dichloromethane
7. 7
   workup.ADDITIONProduct containing fractions
8. 8
   濃縮were concentrated under reduced pressure
9. 9
   workup.ADDITIONtreated with 20% piperidine/dichloromethane (10 mL) for 1 h
10. 10
    濃縮before being concentrated under reduced pressure
11. 11
    その他purified twice via radial chromatography on a 2 mm plate
12. 12
    洗浄eluting with a gradient of 5 to 10% methanol/dichloromethane
13. 13
    その他to provide (200 mg, 37%)

実験手順

To a mixture of the glycine tert-butyl ester hydrogen chloride salt (70) (484 mg, 2.9 mmol) in dichloromethane (25 mL) was added Fmoc-Gly-OH (71) (0.861 mg, 2.99 mmol), DIPEA (756 mg, 4.35 mmol) and HATU (1.3 g, 3.5 mmol). The reaction mixture was stirred at an ambient temperature for 16 h and then poured into ethyl acetate and was washed with water (3×) and brine (1×). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified via radial chromatography on a 2 mm plate eluting with 5% methanol/dichloromethane. Product containing fractions were concentrated under reduced pressure and treated with 20% piperidine/dichloromethane (10 mL) for 1 h, before being concentrated under reduced pressure and then purified twice via radial chromatography on a 2 mm plate eluting with a gradient of 5 to 10% methanol/dichloromethane to provide (200 mg, 37%): 1H-NMR (400 MHz, CDCl3) δ 7.62 (s, 1H), 4.00 (s, 2H), 3.39 (s, 2H), 1.47 (s, 9H).

出典