HCID 68744388, compound → HCID 25064883, compound

HRID 1958730Notes

Reaction equation

HRID 1958730 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:27]=[CH:26][C:12]([C:13]([NH:15][C@@H:16]([CH2:21][N+:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][C:18]([O-:20])=[O:19])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CO>[CH2:8]([C:9]1[CH:27]=[CH:26][C:12]([C:13]([NH:15][C@@H:16]([CH2:21][N+:22]([CH3:23])([CH3:25])[CH3:24])[CH2:17][C:18]([O-:20])=[O:19])=[O:14])=[CH:11][CH:10]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 68744388HCID 68744388, compound

Product 1

HCID 25064883HCID 25064883, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-3-(4-(phenylethynyl)benzamido)-4-(trimethylammonio)butanoate (10 mg, 0.027 mmol) was dissolved into MeOH (1 mL). The solution was treated with 10% Pd/C (0.5 mg). The mixture was stirred under hydrogen at room temperature overnight, and filtered through celite. MeOH was removed under vacuum. The residue was loaded onto a silica gel column and eluted with 4:1 MeOH/DCM to give the title compound as a white powder (2 mg, 22%). 1H NMR (400 MHz, D2O) δ 7.54 (d, 2H, J=8 Hz), 7.22-7.18 (m, 4H), 7.13-7.10 (m, 3H), 4.87-4.81 (m, 1H), 3.65-3.59 (m, 1H), 3.70 (d, 1H, J=13.2 Hz), 3.10 (s, 9H), 2.92-2.85 (m, 4H), 2.46 (d, 2H, J=6.8 Hz); MS ESI 369.2 [M+H]+, calcd for [C22H28N2O3+H]+ 369.22.

Workup

  1. filtrationfiltered through celite
  2. customMeOH was removed under vacuum
  3. washeluted with 4:1 MeOH/DCM

Sources & evidence

ORD record
ord-e63e2111d57f4470a3e4eb743732e093
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

Loading…