HCID 18443269, compound → HCID 18443271, compound

HRID 459174Notes

Reaction equation

HRID 459174 reaction equation
[CH3:1][O:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[CH:9]=1)[C:4]([OH:6])=[O:5]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:24][CH:25]=2)[CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 18443269HCID 18443269, compound

Product 1

HCID 18443271HCID 18443271, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 2-Methoxy-3-{3-[5-(4-phenoxy-phenoxy)-pent-1-ynyl]-phenyl}-propionic acid of Example 155, Step E, and treated with Pd—C (0.1 eq) in ethyl acetate and H2. Filtered through celite and concentrated to give the compound. MS (ES) for C27H30O5 [M+H]+: 435.2, [M+NH4]+: 452.2. 1H-NMR (CDCl3, 200.15 MHz): 7.34–7.19 (m, 3H), 7.09–6.84 (m, 10H), 4.02 (dd, 1H, J=7.5, 4.6), 3.94 (t, 2H, J=6.5), 3.39 (s, 3H), 3.13 (dd, 1H, J=14.0, 4.3), 3.00 (dd, 1H, J=14.0, 7.5), 2.63 (t, 2H, J=7.8), 1.88–1.45 (m, 6H)ppm.

Workup

  1. filtrationFiltered through celite and
  2. concentrationconcentrated
  3. customto give the compound

Sources & evidence

ORD record
ord-77953d2cd63a45489257777495536345
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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