3-Methoxy-4-o-tolylureidophenylacetic acid → HCID 86587780, compound

HRID 350351Notes

Reaction equation

HRID 350351 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][NH:17]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:40][C:41](O)=[O:42])[CH:26]=[CH:27][C:28]=1[NH:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39])=[O:31]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:41](=[O:42])[CH2:40][C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])=[O:31])=[C:23]([O:22][CH3:21])[CH:24]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 16093608HCID 16093608, compound

Product 1

HCID 86587780HCID 86587780, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl (S)-3-methoxy-4-(2-pyrrolidinylmethoxy)benzoate (424 mg, 1.52 mmol) in DMF (8 mL) was added pentafluorphenyl ester of 3-methoxy-4-[N′-(2-methylphenyl) ureido]phenylacetic acid (728 mg, 1.52 mmol) and Et3 N (0.26 mL, 1.87 mmol). And the resulting mixture was stirred at room temp overnight. The mixture was diluted with EtOAc, washed with 1 N HCl, sat. NaHCO3, brine, and dried over MgSO4. The solvent was evaporated off in vacuo and the residue was purified by column chromatography on silica-gel with CHCl3-MeOH (50:1, v/v) as eluent to give 830 mg (95%) ethyl (S)-3-methoxy-4-[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenyl acetyl]-2-pyrrolidinyl methoxy]benzoate as an amorphous solid. 1H-NMR (CDCl3) δ 1.38 (t, 3 H, J=7.3 Hz), 1.88–2.20 (m, 4 H, m), 2.24 (m, 3 H), 3.44–3.50 (m, 1 H), 3.53–3.58 (m, 7 H), 3.82 (s, 3 H), 4.09–4.17 (m, 1 H), 4.22–4.25 (m, 1 H), 4.35 (q, 2 H, J=7.3 Hz), 4.38–4.49 (m, 1 H), 6.71–6.78 (m, 1 H), 6.99 (d, 1 H, J=8.3 Hz), 7.04–7.07 (m, 1H), 7.16–7.19 (m, 2 H), 7.49–7.66 (m, 3 H), 8.06 (d, 1 H, J=8.3 Hz).

Workup

  1. washwashed with 1 N HCl, sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated off in vacuo
  4. customthe residue was purified by column chromatography on silica-gel with CHCl3-MeOH (50:1

Sources & evidence

ORD record
ord-8dc53b402fb34102837fd5fb44e11d23
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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