HCID 25066344, compound → HCID 25066342, compound

HRID 1958758Notes

Reaction equation

HRID 1958758 reaction equation
[CH2:1]([C:7]1[S:11][C:10]([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:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>[Pd]>[CH2:1]([C:7]1[S:11][C:10]([CH2:12][CH2:13][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:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 25066344HCID 25066344, compound

Product 1

HCID 25066342HCID 25066342, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

According to the method described in example S64, (R)-3-(5-((5-hexylthiophen-2-yl)ethynyl)furan-2-carboxamido)-4-(trimethylammonio)butanoate was treated with 10% Pd/C under hydrogen and the product purified to give the title compound as a white powder (14.6 mg, 72%), 1H NMR (400 MHz, D2O) δ 6.85 (br, 1H), 6.32 (br, 1H), 6.21 (br, 1H), 5.65 (br, 1H), 3.64 (m, 1H), 3.41-3.38 (m, 2H), 3.01 (s, 9H), 2.72 (br, 2H), 2.61 (br, 2H), 2.38-2.23 (m, 4H); 1.34 (br, 2H), 1.07 (br, 6H), 0.68 (br, 3H); MS ESI [M+H]+, calcd for [C24H36N2O4S+H]+ 449.25; found m/z 449.3.

Workup

  1. customthe product purified

Sources & evidence

ORD record
ord-5cf92d6c073c4830b9c28f8927b4bad7
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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