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

HRID 492013

반응식

HRID 492013 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-011a1094844c4556ade790fc7abeded8
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531566B2

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