3-Hydroxybenzoic Acid → HCID 13022859, compound

HRID 1178045Notes

Reaction equation

HRID 1178045 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:42]([O:44][C:45](=[O:48])[CH2:46][NH2:47])[CH3:43]>CN(C=O)C.O>[CH2:42]([O:44][C:45](=[O:48])[CH2:46][NH:47][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([OH:10])[CH:12]=1)[CH3:43]

Participants

8

Reactant 5

HCID 74203-Hydroxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 13022859HCID 13022859, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (375 μL, 2.17 mmol) was added drop wise to 3-hydroxy benzoic acid (100 mg, 0.72 mmol) in DMF (4 mL). EDCI (208 mg, 1.09 mmol) and HOBT (117 mg, 0.87 mmol) were added consecutively and after 15 mins, glycine ethyl ester HCl (120 mg, 0.87 mmoles) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford (3-Hydroxy-benzoyl amino)-acetic acid ethyl ester in quantitative yield.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffc5a91789174bc8b238874482a5c280
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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