Hydrochloric Acid → HCID 23077366, compound

HRID 1373505Notes

Reaction equation

HRID 1373505 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:18])[CH2:13][S:14](Br)(=[O:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH2:21])[CH3:20].Cl>O1CCCC1>[CH2:19]([NH:21][S:14]([CH2:13][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:18])(=[O:16])=[O:15])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 23077362HCID 23077362, compound

Product 1

HCID 23077366HCID 23077366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (5 ml) of 1.44 g (3.3 mmol) of 2-(benzyloxycarbonylamino)propane-1-sulfonyl bromide in tetrahydrofuran was added dropwise to 70% aqueous ethylamine solution (10 ml) under ice-cooling. The reaction was carried out at room temperature for 1 hour, after which the reaction mixture was poured into diluted hydrochloric acid, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain crude N-ethyl-2-(benzyloxycarbonylamino)propane-1-sulfonamide, and this crude product was used without further purification in the subsequent reaction.

Workup

  1. temperaturecooling
  2. extractionfollowed by three runs of extraction with ethyl acetate
  3. washThe extract solution was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a306408396274602822cd35e92f4115b
Source dataset
uspto-grants-2007_01
Patent number
US07161032B2

Reaction notes

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