Glycine ethyl ester → HCID 61795720, compound

HRID 2036793Notes

Reaction equation

HRID 2036793 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[CH3:13].C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:17][CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:18])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 12176Glycine ethyl esterHCID 81531DiisopropylethylamineHCID 203244745-Bromopyridine-3-sulfonyl chloride

Product 1

HCID 61795720HCID 61795720, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromopyridine-3-sulfonyl chloride (3.5 g, 14 mmol) (described in the synthesis of Example 170) and glycine ethylester (2.1 g, 20 mmol), diisopropyl ethyl amine (2.6 g, 20 mmol) in THF (70 mL) was stirred at room temperature for 16 h. The reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic solution was separated, dried and evaporated under reduced pressure. The residue was purified using flash column chromatography using ethyl acetate/hexanes as eluent to obtain ethyl 2-(5-bromopyridine-3-sulfonamido)acetate (600 mg, 14%). LCMS Method I: retention time 1.31 min; [M+1]=323, 325.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate
  2. customThe organic solution was separated
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-dc4d0cc30379421e8a627a0edc169eb2
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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