Beta-Alanine → HCID 62958519, compound

HRID 405223Notes

Reaction equation

HRID 405223 reaction equation
[CH3:1]CN(CC)CC.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([OH:17])=O)=[N:13][CH:14]=1.[NH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].CCN=C=NCCCN(C)C>C(Cl)Cl.O.C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([NH:18][CH2:19][CH2:20][C:21]([O:23][CH3:1])=[O:22])=[O:17])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 62958519HCID 62958519, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

Neat Et3N (5.2 mL, 37.5 mmol) was added to a DCM mixture (50 mL) of 5-bromopicolinic acid (5.1 g, 25.0 mmol), beta-alanine mether ester hydrochloride (4.2 g, 30.0 mmol), and EDCI (5.8 g, 30 mmol) and the resulting mixture was stirred at room temperature. After 24 h the resulting mixture was poured into CH2Cl2/H2O (50 mL/50 mL). The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-7c5ad09ff0d743b28ab7fe81750bd81a
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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