HCID 59294360, compound → HCID 25064258, compound

HRID 1958729Notes

Reaction equation

HRID 1958729 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=2)[C:12]([NH:14][C@@H:15]([CH2:20][N+:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][C:17]([O-:19])=[O:18])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd]>[CH2:8]([C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[C:12]([NH:14][C@@H:15]([CH2:20][N+:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][C:17]([O-:19])=[O:18])=[O:13])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 59294360HCID 59294360, compound

Product 1

HCID 25064258HCID 25064258, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

According to the method described in example S64, (R)-3-(3-(phenylethynyl)-benzamido)-4-(trimethylammonio)butanoate was treated with 10% Pd/C under hydrogen and the product purified to give the title compound as a white powder (7.2 mg, 89%). 1H NMR (400 MHz, D2O) δ 7.41 (d, 1H, J=8 Hz), 7.34 (s, 1H), 7.07 (t, 1H, J=8 Hz), 7.02-6.90 (m, 4H), 6.86 (d, 2H, J=8 Hz), 4.76 (m, 1H), 3.60-3.54 (m, 1H), 3.41 (d, 1H, J=13.2 Hz), 3.00 (s, 9H), 2.61 (br, 4H), 2.41-2.28 (m, 2H); MS ESI 369.2 [M+H]+, calcd for [C22H28N2O3+H]+ 369.22.

Workup

  1. customthe product purified

Sources & evidence

ORD record
ord-00a844cc93e447178961be7b2784fd49
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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