HCID 46205447, compound → HCID 46205448, compound

HRID 2366463Notes

Reaction equation

HRID 2366463 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(O)(=O)C.[Pt]>[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 46205447HCID 46205447, compound

Product 1

HCID 46205448HCID 46205448, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of EXAMPLE 50B (5.5 g) and 5% Pt/C (20 mg) in acetic acid (200 mL) was hydrogenated at 60 psi for 12 hours and filtered. The filtrate was concentrated and the concentrate partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was isolated and concentrated. The concentrate was flash chromatographed on silica gel with 10-30% ethyl acetate/hexanes.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe concentrate partitioned between ethyl acetate and sodium bicarbonate solution
  4. customThe organic phase was isolated
  5. concentrationconcentrated
  6. customchromatographed on silica gel with 10-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-642bf2f3de7545cf81e1e6a89a44a7e0
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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