4-(((Tert-butoxy)carbonyl)amino)butanoic acid → HCID 58743831, compound

HRID 388856Notes

Reaction equation

HRID 388856 reaction equation
S(Cl)([O:4][CH2:5][Cl:6])(=O)=O.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])=[O:14])([CH3:11])([CH3:10])[CH3:9].C([O-])(O)=O.[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O.C(Cl)Cl>[Cl:6][CH2:5][O:4][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][NH:15][C:13]([O:12][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:14]

Participants

6

Reactant 3

HCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 58743831HCID 58743831, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 21908982Water methylene chlorideSolvent

Procedure

To a mixture of chloromethyl chlorosulfate (1.1 equivalent) and 4-tert-Butoxycarbonylamino-butyric acid (1 equivalent) was added NaHCO3 (3.6 equivalents) and Bu4NHSO4 (catalytic amount) in water/CH2Cl2 (1:1). The mixture was stirred at room temperature overnight. The organic phase was thereafter separated and the aqueous phase was extracted with CH2Cl2 (three times). The combined organic layer was washed with NaHCO3 (×3), brine (×3), dried with MgSO4, filtered and evaporated.

Workup

  1. customThe organic phase was thereafter separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (three times)
  3. washThe combined organic layer was washed with NaHCO3 (×3), brine (×3)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9b5e51aec7a848aaa241faa64a861cec
Source dataset
uspto-grants-2013_02
Patent number
US08377990B2

Reaction notes

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