Sulfuric Acid → (S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

HRID 1957587Notes

Reaction equation

HRID 1957587 reaction equation
[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][NH2:16])[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[CH3:22][C:23](=[CH2:25])[CH3:24].[ClH:26].CCOCC>C(Cl)(Cl)Cl.COCCOC>[ClH:26].[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][NH2:16])[C:12]([O:14][C:23]([CH3:25])([CH3:24])[CH3:22])=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic AcidHCID 10953452Ether hydrochloride

Product 1

HCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-78 °C

Procedure

In a Fischer-Porter tube, a mixture of 7-9 (10.2 g, 42 mmol) and DME (150 mL) was sequentially, treated with H2SO4 (6.4 mL, 0.12 mol), cooled to -78° C., and then condensed isobutylene (75 mL). The cooling both removed. After 2h, ice/water (250 mL) was added followed by washing with ether (2×). The aqueous phase was basified with aq 6N NaOH, then saturated with NaCl followed by extraction with EtOH (3×). The combined extracts were washed with brine, dried (MgSO4), and concentrated to give a white solid. This was dissolved in CHCl3 then treated with 1N HCl/ether (22 mL) then concentrated to give 7-4 as a glossy yellow solid.

Workup

  1. washby washing with ether (2×)
  2. extractionsaturated with NaCl followed by extraction with EtOH (3×)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a white solid
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-4b1be881e36b4c2f88a0fee84995aed8
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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