Methanol → HCID 15177225, compound

HRID 1493844Notes

Reaction equation

HRID 1493844 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](C#CP(OC)(C[C@@H](O)CC(OC)=O)=O)=[C:10]([CH:17]([CH3:19])[CH3:18])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:4][CH:3]=1.CO.[CH3:36][CH2:37][O:38][C:39](C)=[O:40]>[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:39]([O:38][CH2:37][CH3:36])=[O:40])=[C:10]([CH:17]([CH3:19])[CH3:18])[N:11]3[C:16]=2[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 131716913HCID 131716913, compound

Product 1

HCID 15177225HCID 15177225, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of Example 1, Part C compound 6.50 g, 20.0 mmol) in EtOAc (35 mL)-CH3OH (70 mL) was added 10% Pd-C (1.5 g) and the resulting mixture hydrogenated in a Parr apparatus at 50 psi for 20 hours. The catalyst was removed by filtration through Celite and the filtrate evaporated to a colorless, viscous oil. The crude product was crystallized from hexane to give pure title compound (6.292 g, 96%) as white crystals, mp 85.5°-86.5° C.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe filtrate evaporated to a colorless, viscous oil
  3. customThe crude product was crystallized from hexane

Sources & evidence

ORD record
ord-fc1aacb8843045cb8b1bf3819b2ece61
Source dataset
uspto-grants-1991_06
Patent number
US05025000

Reaction notes

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