HCID 18443225, compound → HCID 58822718, compound

HRID 459143Notes

Reaction equation

HRID 459143 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([O:22][CH3:23])[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([O:22][CH3:23])[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 18443225HCID 18443225, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58822718HCID 58822718, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared as follows: (2S) 3-{4-[3-(Biphenyl-4-yloxy)-prop-1-ynyl]-phenyl}-2-methoxy-propionic acid (0, Step C) (0.0325 g, 0.08 mmol) was dissolved in methanol (10 mL). Palladium 10% an activated carbon (0.004 g, 0.004 mmol) was added and the solution saturated with hydrogen (1 Atm) and stirred for 5 hours. The mixture was filtered through a pad of celite and concentrated under vacuum. The residue was purified by column chromatography (silica gel, hexanes/Ethyl acetate-Acetic acid 50:50:1, Rf0.23) (85%). 1H-NMR (CDCl3, 200.15 MHz): δ 7.56–7.24 (m, 11H), 6.94 (d, 2H, J=8.8), 4.02–3.95 (m, 3H), 3.38 (s, 3H), 3.11 (dd, 1H, J=14.3, 4.4), 2.98 (dd, 1H, J=14.3, 7.3), 2.79 (t, 2H, J=8.1), 2.16–2.03 (m, 3H). MS (ES) for C25H26O4 [M+NH4]+: 408.2, [M+Na]+: 413.2.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by column chromatography (silica gel, hexanes/Ethyl acetate-Acetic acid 50:50:1, Rf0.23) (85%)

Sources & evidence

ORD record
ord-bc9b4361448841c99d111c4a6838902f
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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