HCID 68529891, compound → HCID 68529942, compound

HRID 2246552Notes

Reaction equation

HRID 2246552 reaction equation
C([O:8][C:9](=[O:59])[CH:10]([NH:23][C:24](=[O:58])[CH2:25][CH2:26][Si:27]([CH2:30][CH2:31][C:32]1[C:44]2[CH2:43][N:42]3[C:37](=[CH:38][C:39]4[C:49]([CH2:51][CH3:52])([OH:50])[C:48](=[O:53])[O:47][CH2:46][C:40]=4[C:41]3=[O:45])[C:36]=2[N:35]=[C:34]2[CH:54]=[CH:55][CH:56]=[CH:57][C:33]=12)([CH3:29])[CH3:28])[CH2:11][CH2:12][C:13]([O:15]CC1C=CC=CC=1)=[O:14])C1C=CC=CC=1>C(COC)OC.C(O)C.[Pd]>[CH2:51]([C:49]1([OH:50])[C:39]2[CH:38]=[C:37]3[N:42]([C:41](=[O:45])[C:40]=2[CH2:46][O:47][C:48]1=[O:53])[CH2:43][C:44]1[C:32]([CH2:31][CH2:30][Si:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][C:24]([NH:23][CH:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:9]([OH:59])=[O:8])=[O:58])=[C:33]2[CH:57]=[CH:56][CH:55]=[CH:54][C:34]2=[N:35][C:36]3=1)[CH3:52]

Participants

5

Reactant 1

HCID 68529891HCID 68529891, compound

Product 1

HCID 68529942HCID 68529942, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of Compound 49 (25 mg) in dimethoxyethane (1 ml) and ethanol (1 ml) was added 10% palladium on charcoal (10 mg). The mixture was stirred under hydrogen balloon pressure for 16 hours at room temperature. The resulted mixture was filtrated through Celite and the solvents were removed by rotary evaporation. The residue was purified by prepared TLC plate, eluting with methanol/dichloromethane (50/50), to afford Compound 50 as a yellow solid.

Workup

  1. filtrationThe resulted mixture was filtrated through Celite
  2. customthe solvents were removed by rotary evaporation
  3. customThe residue was purified
  4. customby prepared TLC plate
  5. washeluting with methanol/dichloromethane (50/50)

Sources & evidence

ORD record
ord-64a27398011e4f76938c5ce661a7792a
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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