HCID 25066338, compound → HCID 59294362, compound

HRID 1958759Notes

Reaction equation

HRID 1958759 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[O:18][C:17]([C:19]([NH:21][C@@H:22]([CH2:27][N+:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][C:24]([O-:26])=[O:25])=[O:20])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]>[Pd]>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]2[O:18][CH:17]([C:19]([NH:21][C@@H:22]([CH2:27][N+:28]([CH3:31])([CH3:29])[CH3:30])[CH2:23][C:24]([O-:26])=[O:25])=[O:20])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 1

HCID 25066338HCID 25066338, compound

Product 1

HCID 59294362HCID 59294362, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

According to the method described in example S64, (R)-3-(5-((4-pentylphenyl)ethynyl)furan-2-carboxamido)-4-(trimethylammonio)butanoate was treated with 10% Pd/C under hydrogen overnight and the product purified to give the title compound as a white powder (16.5 mg, 48%). 1H NMR (400 MHz, D2O) δ 6.86 (d, 2H, J=8.2 Hz), 6.75 (d, 2H, J=7.6 Hz), 4.60-4.53 (m, 1H), 4.08-4.01 (m, 1H), 3.61-3.36 (m, 3H), 3.02 (s, 9H), 2.45-2.32 (m, 6H), 1.87-1.50 (m, 5H), 1.35-1.27 (m, 2H), 1.25-1.05 (m, 5H), 0.60-0.55 (m, 3H); MS ESI [M+H]+, calcd for [C25H40N2O4+H]+ 433.31; found m/z 433.3.

Workup

  1. customthe product purified

Sources & evidence

ORD record
ord-b535a04a1efb40c99cd79baf65f6e19b
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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