HCID 86708058, compound → HCID 86708060, compound

HRID 1524358Notes

Reaction equation

HRID 1524358 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C@@H:25]([CH2:35]/[CH:36]=[CH:37]/[CH:38]=[O:39])[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:18])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O.C(O)C.[OH-].[OH-].[Pd+2]>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C@@H:25]([CH2:35][CH2:36][CH2:37][CH:38]=[O:39])[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:17])=[O:18])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86708058HCID 86708058, compound

Product 1

HCID 86708060HCID 86708060, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of the material from Step 4 (7.2 g, 12.04 mmol) in (1:1) EtOAc-ethanol (232 mL) was degassed with nitrogen, and 20% palladium hydroxide on carbon (0.72 g, 1.03 mmol) was added. The reaction mixture was stirred under hydrogen (1 atm) for 2 hours. The reaction mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 4 g of the title compound. 1H NMR (DMSO-d6): δ 9.60 (s, 1H), 7.79 (d, J=7.96 Hz, 2H), 7.50 (d, J=7.99 Hz, 2H), 4.79 (s, 2H), 3.68-3.60 (m, 1H), 3.45 (t, J=20.48 Hz, 2H), 3.23-3.09 (m, 1H), 3.08-2.98 (m, 1H), 2.37 (d, J=7.09 Hz, 2H), 1.62-1.06 (m, 10H), 0.91 (s, 9H), 0.84 (t, J=6.94 Hz, 3H), 0.80 (s, 9H), 0.09 (s, 6H), −0.06 (s, 6H).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4d1fc7ffd011457e8d96282181fbf6a5
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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