반응 #681370

반응 방정식

glycine tert-butyl ester hydrogen chloride salt

Fmoc-Gly-OH

DIPEA

HATU

→

tert-butyl 2-(2-aminoacetamido)acetate

용매

ethyl acetate

dichloromethane

반응 조건

후처리

1. 1
   세척was washed with water (3×) and brine (1×)
2. 2
   건조The organic phase was dried over MgSO4
3. 3
   여과filtered
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The resulting residue was purified via radial chromatography on a 2 mm plate
6. 6
   세척eluting with 5% methanol/dichloromethane
7. 7
   workup.ADDITIONProduct containing fractions
8. 8
   농축were concentrated under reduced pressure
9. 9
   workup.ADDITIONtreated with 20% piperidine/dichloromethane (10 mL) for 1 h
10. 10
    농축before being concentrated under reduced pressure
11. 11
    기타purified twice via radial chromatography on a 2 mm plate
12. 12
    세척eluting with a gradient of 5 to 10% methanol/dichloromethane
13. 13
    기타to provide (200 mg, 37%)

실험 절차

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).

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