4-Hydroxybenzoic Acid → HCID 10846723, compound

HRID 1178043Notes

Reaction equation

HRID 1178043 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.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:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([OH:10])=[CH:19][CH:18]=1)[CH3:43]

Participants

8

Reactant 5

HCID 1354-Hydroxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 10846723HCID 10846723, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (1.4 g, 10.86 mmol) was added drop wise to 4-hydroxy benzoic acid (500 mg, 3.62 mmol) in DMF (10 mL). EDCI (1.7 g, 9.05 mmol) and HOBT (586 mg, 4.34 mmol) were added consecutively and, after 15 minutes, glycine ethyl ester HCl (603 mg, 4.344 mmol) 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 (4-hydroxy-benzoyl amino)-acetic acid ethyl ester in 91% 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-349935b947d14b8099986bcd55969f38
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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