反応 #45252

反応方程式

chlorosulfonyl isocyanate

2-methyl-propan-2-ol

glycine ethyl ester

Et3N

HCl

→

ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate

収率 85.0%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   その他did not rise above 5° C
2. 2
   その他didn't rise above 5° C
3. 3
   workup.ADDITIONWhen the addition
4. 4
   workup.STIRRINGstirred overnight
5. 5
   抽出extracted with CH2Cl2
6. 6
   洗浄The organic layer was washed with saturated NaCl
7. 7
   乾燥dried (Mg2SO4)
8. 8
   ろ過filtered
9. 9
   その他After removal of the solvent
10. 10
    洗浄the crude product was washed with CH2Cl2

実験手順

To a stirred solution of chlorosulfonyl isocyanate (1.43 g, 10.0 mmol) in CH2Cl2 (20 mL) at 0° C. was added 2-methyl-propan-2-ol (0.74 g, 10.0 mmol) at such a rate that the reaction solution temperature did not rise above 5° C. After being stirred for 1.5 h, a solution of glycine ethyl ester (1.45 g, 12.0 mmol) and Et3N (3.2 mL, 25.0 mmol) in CH2Cl2 (20 mL) was added at such a rate that the reaction temperature didn't rise above 5° C. When the addition was completed, the solution was warmed to RT and stirred overnight. The reaction mixture was poured into 10% HCl and extracted with CH2Cl2. The organic layer was washed with saturated NaCl, dried (Mg2SO4) and filtered. After removal of the solvent, the crude product was washed with CH2Cl2 to afford ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate (2.4 g, 85%). 1H-NMR (DMSO): δ 10.85 (s, 1H), 8.04 (t, J=6.0 Hz, 1H), 4.07 (q, J=5.6 Hz, 2H), 3.77 (d, J=6.0 Hz, 2H), 1.40 (s, 9H), 1.18 (t, J=7.2 Hz, 3H).

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