HCID 57989068, compound → HCID 57988899, compound

HRID 471296Notes

Reaction equation

HRID 471296 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:21][NH:22][C@H:23]([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][OH:32])[CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[Si:35]([O:34][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][C@H:23]([CH3:33])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][OH:32])[CH:26]=1)([C:38]([CH3:41])([CH3:39])[CH3:40])([CH3:37])[CH3:36]

Participants

5

Reactant 2

HCID 57989068HCID 57989068, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57988899HCID 57988899, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-(benzyloxy)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-((R)-1-(3-(hydroxymethyl)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one (Example 276, step e) (0.52 g) and 10% palladium on carbon catalyst (0.102 g) in ethanol (36 mL) was hydrogenated at room temperature and at 5 bar pressure of hydrogen for 1.5 hours, then hydrogenated at room temperature and at 1 bar pressure of hydrogen overnight. The mixture was filtered through diatomaceous earth, washing the catalyst well with ethanol, and the combined filtrate and washings were concentrated in vacuo to afford the subtitled compound. Yield 0.42 g. Material used immediately in the next step.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washwashing the catalyst well with ethanol
  3. concentrationthe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-9f790f9784514b6c80b96fd42ba68f21
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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