Hydrochloric Acid → ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate

HRID 492005

反応式

HRID 492005 の反応式
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].C[C:9]([OH:12])([CH3:11])C.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14].[CH3:20][CH2:21]N(CC)CC.Cl>C(Cl)Cl>[CH2:9]([O:12][C:6]([NH:5][S:2]([NH:18][CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:19])(=[O:4])=[O:3])=[O:7])[CH2:11][CH2:20][CH3:21]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 8471TriethylamineHCID 12176Glycine ethyl esterHCID 70918Chlorosulfonyl isocyanate

生成物 1

HCID 18449914ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

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).

後処理

  1. customdid not rise above 5° C
  2. customdidn't rise above 5° C
  3. additionWhen the addition
  4. stirringstirred overnight
  5. extractionextracted with CH2Cl2
  6. washThe organic layer was washed with saturated NaCl
  7. dry with materialdried (Mg2SO4)
  8. filtrationfiltered
  9. customAfter removal of the solvent
  10. washthe crude product was washed with CH2Cl2

出典と根拠

ORDレコード
ord-9962f518ab984bd5a09ba6f4b99e43cd
出典データセット
uspto-grants-2009_05
特許番号
US07531566B2

関連ノート

読み込み中…