Sodium Acetate → HCID 71291709, compound

HRID 1746447Notes

Reaction equation

HRID 1746447 reaction equation
Cl[C:2]1[S:3][C:4]([C:7]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([O:24][CH3:25])=[C:17]([O:22][CH3:23])[CH:18]=3)[CH:13]=2)([OH:11])[CH:8]([CH3:10])[CH3:9])=[CH:5][N:6]=1.C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[CH3:23][O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:24][CH3:25])[CH:13]=[C:12]([C:7]([C:4]1[S:3][CH:2]=[N:6][CH:5]=1)([OH:11])[CH:8]([CH3:10])[CH3:9])[CH:21]=[CH:20]2

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 71291698HCID 71291698, compound

Product 1

HCID 71291709HCID 71291709, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of alcohol 1 (0.07 g, 0.18 mmol) in ethanol (10 mL) were added sodium acetate (10 mg, 0.12 mmol) followed by addition of 10% Pd/C (60 mg) at RT under inert atmosphere. The reaction mixture was stirred at RT for 2 h under H2 atmosphere (30 psi). Progress of reaction was monitored by TLC. The reaction mixture was filtered through a pad of celite and celite bed was washed with ethanol (2×10 mL). The filtrate was concentrated under reduced pressure to afford 2 (50 mg, 0.15 mmol, 78%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.75 (s, 1H), 7.88 (s, 1H), 7.85 (s, 1H), 7.65 (d, J=8.5 Hz, 1H), 7.41 (d, J=8.5 Hz, 1H), 7.13 (s, 1H), 7.09 (s, 1H), 3.99 (s, 6H), 2.84-2.78 (m, 1H), 1.06 (d, J=6.5 Hz, 3H), 0.87 (d, J=6.5 Hz, 3H). Mass: m/z: 344 [M+1]. HPLC: 99.65%.

Workup

  1. customProgress of reaction
  2. filtrationThe reaction mixture was filtered through a pad of celite and celite bed
  3. washwas washed with ethanol (2×10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ecf65400ba834e5c81ee195a63a2598c
Source dataset
uspto-grants-2015_10
Patent number
US09150527B2

Reaction notes

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