Hydroxyphenylacetic acid → HCID 54921034, compound

HRID 1178066Notes

Reaction equation

HRID 1178066 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:44]([O:46][C:47](=[O:50])[CH2:48][NH2:49])[CH3:45]>CN(C=O)C.O>[CH2:44]([O:46][C:47](=[O:50])[CH2:48][NH:49][C:18](=[O:20])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([OH:10])=[CH:16][CH:15]=1)[CH3:45]

Participants

8

Reactant 5

HCID 127Hydroxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54921034HCID 54921034, compoundYield 106.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (441 mg, 0.6 ml, 3.41 mmol) was added to a stirred solution of 4-hydroxyphenyl acetic acid (104 mg, 0.68 mmol) in DMF (4 mL). HOBT (101 mg, 0.748 mmol) and EDCI.HCl (245 mg, 1.28 mmol) were added at room temperature. After 2 minutes glycine ethyl ester hydrochloride (114.5 mg, 0.82 mmol) was added. The resulting mixture was stirred at room temperature for 24 hours. 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 172 mg of [2-(4-hydroxy-phenyl)-acetyl amino]-acetic acid ethyl ester). LC-MS purity: 81.298%, HPLC purity 93.36%. 1H NMR (CDCl3): δ 7.1 (d, 2H), 6.8 (d, 2H), 6.0 (bs, 1H), 4.15 (q, 2H), 4.0 (d, 2H), 3.5 (s, 2H), 1.2 (t, 3H).

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-8d427e161edf44a4b171aaf40ad2b39e
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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