3-{4-[4-(2-Tert-butoxycarbonylamino-2-carboxy-ethyl)-phenoxy]-phenyl}-acrylic acid methyl ester → 2-Tert-butoxycarbonylamino-3-{4-[4-(2-methoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionic acid

HRID 748976Notes

Reaction equation

HRID 748976 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[H][H]>[Ni].CO>[C:28]([O:27][C:25]([NH:24][CH:20]([CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:32])=[CH:11][CH:10]=2)=[CH:14][CH:15]=1)[C:21]([OH:23])=[O:22])=[O:26])([CH3:30])([CH3:31])[CH3:29]

Participants

5

Reactant 2

HCID 692305483-{4-[4-(2-Tert-butoxycarbonylamino-2-carboxy-ethyl)-phenoxy]-phenyl}-acrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 597628022-Tert-butoxycarbonylamino-3-{4-[4-(2-methoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionic acidYield 55%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel 2800 (15.4 g) was added to a degassed solution of the unsaturated ester 3 (14.7 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. Flash chromatography (30-50% ethyl acetate in hexane containing 1% acetic acid) of the resulting residue gave the desired saturated ester 4 (8.1 g, 55%). 1H NMR (400 MHz, DMSO-d6): 12.7 (br, 1H), 7.22 (overlapped d, J=8.4 Hz, 4H), 7.08 (d, J=8.0 Hz, 1H), 6.88 (overlapped d, J=8.0 Hz, 4H), 4.07 (br, 1H), 3.00 (m, 1H), 2.82 (t, J=7.6 Hz, 2H), 2.79 (m, 1H), 2.62 (t, J=8.0 Hz, 2H), 1.33 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-8e820ab3e84042deb427ec9d827489fb
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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