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

HRID 16974

Reaction equation

HRID 16974 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a3e6e6c72fdd44fab0a361edc472f42e
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Linked notes

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