3-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl ester → 3-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-propionic acid methyl ester

HRID 749002Notes

Reaction equation

HRID 749002 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[H][H]>[Ni].CO>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 692266383-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 597511053-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-propionic acid methyl esterYield 75.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel 2800 (21.9 g) was added to a degassed solution of the unsaturated ester 30 (20.0 g) in MeOH (100 mL) and the resulting suspension was treated with hydrogen at atmospheric pressure for 18 h. The suspension was filtered over a Celite® bed and concentrated. Completion of hydrogenation was determined by NMR. Flash chromatography (20-50% ethyl acetate in hexane containing 1% acetic acid) of the resulting residue gave the desired saturated ester 31 (15.1 g, 75%). 1H NMR (400 MHz, DMSO-d6): 12.8 (br, 1H), 7.37 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.4 Hz, 4H), 3.59 (s, 3H), 2.84 (t, J=7.6 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H) 1.39 (s, 9H).

Workup

  1. filtrationThe suspension was filtered over a Celite® bed
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-87b16f5e3b7748498a2bfae7e5f6d803
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

Loading…