3-[4-Benzyloxy-2-(2-tert-butoxycarbonylamino-ethyl)-phenyl]-acrylic acid methyl ester → 3-[2-(2-Tert-butoxycarbonylamino-ethyl)-4-hydroxy-phenyl]-propionic acid methyl ester

HRID 1181084Notes

Reaction equation

HRID 1181084 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][C:7]=1[CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[H][H]>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24]

Participants

6

Reactant 2

HCID 692316053-[4-Benzyloxy-2-(2-tert-butoxycarbonylamino-ethyl)-phenyl]-acrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 589793153-[2-(2-Tert-butoxycarbonylamino-ethyl)-4-hydroxy-phenyl]-propionic acid methyl esterYield 36.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[4-benzyloxy-2-(2-tert-butoxycarbonylamino-ethyl)-phenyl]-acrylic acid methyl ester (4.15 g, 10.1 mmol) in THF (100 mL) and MeOH (10 mL) was added 5% Pd—C (200 mg) in THF (10 mL). The resulting suspension was treated with hydrogen under balloon pressure for 18 h. The mixture was filtered through a pad of Celite and concentrated. The residue was purified by silica gel chromatography (EtOAc/hexanes, 6/4) to afford the title compound (1.20 g, 34%). 1H NMR (400 MHz, CDCl3): δ 1.44 (s, 9H), 2.57 (t, 2H, J=7.8 Hz), 2.77 (t, 2H, J=7.3 Hz), 2.88 (t, 2H, J=7.8 Hz), 3.33 (br s, 2H), 3.68 (s, 3H), 6.65 (br s, 1H), 6.67 (d, 1H, J=8.3 Hz), 7.02 (d, 1H, J=8.3 Hz). MS (ES+) m/z 324.1 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (EtOAc/hexanes, 6/4)

Sources & evidence

ORD record
ord-4e59ccfb7ead4765b5623c02ace9dfc8
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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