HCID 67608904, compound → HCID 67608619, compound

HRID 1965200Notes

Reaction equation

HRID 1965200 reaction equation
C(O[C:9](=O)[N:10]([CH:12]([C:14](=[O:48])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[N:28]([C:42](=[O:47])[NH:43][CH:44]([CH3:46])[CH3:45])[CH2:29][CH:30]([O:31][C:32](=[O:41])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:24]12)=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])C)C1C=CC=CC=1>CO>[CH3:20][C:17]([CH3:18])([CH3:19])[CH:16]([NH:15][C:14](=[O:48])[CH:12]([NH:10][CH3:9])[CH3:13])[C:21]([N:23]1[CH:24]2[CH:25]([N:28]([C:42](=[O:47])[NH:43][CH:44]([CH3:46])[CH3:45])[CH2:29][CH:30]2[O:31][C:32](=[O:41])[NH:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:26][CH2:27]1)=[O:22]

Participants

3

Reactant 1

HCID 67608904HCID 67608904, compound

Product 1

HCID 67608619HCID 67608619, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 58 (250 mg, 0.37 mmol) and 10% Pd-on-carbon (wet, 100 mg, 0.10 mmol) in MeOH (10 mL) was stirred vigorously under an atmosphere of H2. After 3.5 h, the catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe filter and the solvent was removed in vacuo. The crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 20-80% MeOH/water containing 0.1% HOAc over 25 min; Flow: 40 mL/min). The product-containing fractions were combined and lyophilized to provide 59 (130 mg, 65%) as a flocculent white powder.

Workup

  1. customthe catalyst was removed by filtration with an Acrodisc® 0.45 μm nylon membrane syringe
  2. filtrationfilter
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by reverse-phase HPLC (2″ Dynamax® C18, 20-80% MeOH/water containing 0.1% HOAc over 25 min

Sources & evidence

ORD record
ord-8724fa29ec804986a06fcf0043b360d3
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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