Acetic acid ethanol → HCID 69333117, compound

HRID 354320Notes

Reaction equation

HRID 354320 reaction equation
C([O:8][CH:9]1[CH2:13][N:12]([C:14](=[O:35])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[O:24])=[C:18]([O:33][CH3:34])[CH:17]=2)[CH:11]([CH2:36][O:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([O-:44])=[O:43])=[CH:40][C:39]=2[O:47][CH3:48])[CH2:10]1)C1C=CC=CC=1.[CH3:49][C:50](O)=O.CCO>[Pd]>[OH:8][CH:9]1[CH2:13][N:12]([C:14](=[O:35])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[O:24])=[C:18]([O:33][CH3:34])[CH:17]=2)[CH:11]([CH2:36][O:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([O:44][CH2:49][CH3:50])=[O:43])=[CH:40][C:39]=2[O:47][CH3:48])[CH2:10]1

Participants

4

Reactant 2

HCID 18476134Acetic acid ethanolHCID 86587782HCID 86587782, compound

Product 1

HCID 69333117HCID 69333117, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A stirred mixture of 4-[4-benzyloxy-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]-3-methoxybenzoate (440 mg, 0.645 mmol) and 5% Pd/C (400 mg) in AcOH:EtOH (1:1, v/v, 100 mL) was hydrogenated at 1 atm for 5 hr. The mixture was filtered to remove the catalyst and the filtrate was concentrated in vacuo. The residue was chromatographed on silica-gel with CHCl3:EtOH (10:1, v/v) as eluent to give 90 mg (24%) ethyl 4-[4-hydroxy-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]-3-methoxybenzoate as a pale yellow oil. 1H-NMR (CDCl3) δ1.39 (3 H, t, J=7.3 Hz), 2.04-2.37 (total 5 H, m), 3.44-4.70 (16 H, series of m), 6.63 (1 H, s), 6.70-6.80 (2 H, m), 6.84 (1 H, d, j=8.3 Hz), 7.11 (1 H, t, J=7.8 Hz), 7.20-7.24(3 H, m), 7.45 (1 H, d, J=2.0 Hz), 7.59 (2 H, dd, J=8.3, 2.0 Hz), 8.01 (1 H, d, J=7.8 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica-gel with CHCl3:EtOH (10:1

Sources & evidence

ORD record
ord-13fc30d22ba7491e9180a43dd63b8ddb
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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