Acetic Acid → HCID 10648298, compound

HRID 1061312Notes

Reaction equation

HRID 1061312 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)OCC1.[NH2:22][CH2:23][C@@H:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=1)[OH:25].C(O)(=O)C>CO.[Pd]>[OH:25][C@H:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=1)[CH2:23][NH:22][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10637170HCID 10637170, compoundHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 10648298HCID 10648298, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (E)-3-[4-(4-oxo-piperidine-1-yl)-phenyl]-acrylic acid (which was obtained in Example 170) (0.10 g, 0.40 mmol) and N-[5-((1R)-2-Amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methane-sulfonamide (which was obtained in Example 10) (0.12 g, 0.48 mmol) in methanol (15 mL) was treated with acetic acid (0.03 g, 0.5 mmol), and 0.05 g of 10% Pd/C. The mixture was hydrogenated at 25 psi for 24 h, and then filtered through Celite and evaporated. The residue was triturated with ether to give 0.18 g of an off-white solid; m.p. 130-133° C.; 1H NMR (DMSO-d6) δ 1.30-1.46 (m, 2H), 1.84-1.95 (m, 2H), 2.37-2.50 (m, 4H), 2.60-2.78 (m, 4H), 2.92 (s, 3 H), 3.53-3.62 (m, 3H), 4.46-4.55 (m, 1H), 6.85 (d, 2H), 6.92-7.10 (m, 4H), 7.18 (dd, 1H); MS (ES) m/z: 478.3 (MH+).

Workup

  1. filtrationfiltered through Celite
  2. customevaporated
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-90ce94ef53294e44948948301ac60d10
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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