4-Phenoxybenzoic acid → HCID 27000073, compound

HRID 1178023Notes

Reaction equation

HRID 1178023 reaction equation
CCN(C(C)C)C(C)C.[O:10]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:49]([O:51][C:52](=[O:55])[CH2:53][NH2:54])[CH3:50]>CN(C=O)C.O>[CH2:49]([O:51][C:52](=[O:55])[CH2:53][NH:54][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:25][CH:24]=1)[CH3:50]

Participants

8

Reactant 5

HCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 27000073HCID 27000073, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (12.1 g, 16.2 mL, 93.6 mmol) was added to a stirred solution of 4-phenoxy benzoic acid (4.011 g, 18.73 mmol) in DMF (40 mL). HOBT (2.78 g, 20.57 mmol) and EDCI.HCl (9 g, 47 mmol) were then added. After 2 minutes, glycine ethyl ester hydrochloride (3.14 g, 22.5 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with cold water and the product extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 5.73 g of (4-phenoxy-benzoylamino)-acetic acid ethyl ester as a white powder. 1H NMR (DMSO): δ 8.85 (t, 1H), 7.85 (d, 2H), 7.4 (t, 2H), 7.2 (t, 1H), 7.0 (m, 4H), 4.1 (q, 2H), 3.9 (d, 2H), 1.2 (t, 3H).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bd28e785492440a99729c5b094ba938
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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