Diethyl Ether → HCID 22501877, compound

HRID 1633896Notes

Reaction equation

HRID 1633896 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl.[CH2:23]([O:25][C:26](=[O:30])[CH2:27][CH2:28][NH2:29])[CH3:24].C(OCC)C>C(Cl)Cl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:29][CH2:28][CH2:27][C:26]([O:25][CH2:23][CH3:24])=[O:30])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 22501877HCID 22501877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 4-bromomethylphenylsulfonylchloride (10 g, 37 mmol) in CH2Cl2 (200 mL) at 0° C. was added diisopropylethylamine (16 mL, 93 mmol) followed by ethyl-3-aminopropionate hydrochloride (5.1 g, 37 mmol)). The reaction was stirred for 10 minutes at 0° C. and the solvent was evaporated at room temperature under reduced pressure. The residue was dissolved in ethyl acetate and washed with 1N HCl (3×), H2O, aqueous NaHCO3 (3×), brine (3×) and dried over MgSO4. The solvent was concentrated to give a syrup. Addition of ethyl ether induced crystallization of the product as a white solid (10 g, 30 mmol, 81%).

Workup

  1. customthe solvent was evaporated at room temperature under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N HCl (3×), H2O, aqueous NaHCO3 (3×), brine (3×)
  4. dry with materialdried over MgSO4
  5. concentrationThe solvent was concentrated
  6. customto give a syrup

Sources & evidence

ORD record
ord-63d31128e93d4a17ae4a807e8e3559cc
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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