HCID 131728342, compound → HCID 68506130, compound

HRID 1715447Notes

Reaction equation

HRID 1715447 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:10]([CH:11]=[C:12]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][O:36][C:37]4[C:42]([F:43])=[CH:41][CH:40]=[C:39]([F:44])[C:38]=4[Cl:45])=[CH:29][CH:28]=3)[CH:13]2[C:24]([OH:26])=[O:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]([CH2:11][CH:12]([C:27]3[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH2:35][O:36][C:37]4[C:42]([F:43])=[CH:41][CH:40]=[C:39]([F:44])[C:38]=4[Cl:45])=[CH:31][CH:32]=3)[CH:13]2[C:24]([OH:26])=[O:25])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 131728342HCID 131728342, compound

Product 1

HCID 68506130HCID 68506130, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 250 mL round-bottom flask equipped with a magnetic stirrer is suspended compound B1 (1.17 g, 1.80 mmol) and Pd/C (10% w/w, 1.20 g) in MeOH (100 mL). The resulting suspension is deoxygenated and then flushed with H2 gas for 15 min. Finally, the reaction mixture is vigorously stirred at rt under a static H2 atmosphere maintained with a balloon. After 2 h, quantitative consumption of compound B1 can be discerned. The reaction vessel is then vigorously purged with N2 and the suspension is filtered through a bed of Celite and SiO2. After washing the insolubles with copious quantities of CH2Cl2 and EtOAc, the filtrate is concentrated in vacuo to the title compound as a mixture of four diastereomers (1.116 g, 95% crude yield, ES−=648.9). This material is used further without purification.

Workup

  1. customIn a 250 mL round-bottom flask equipped with a magnetic stirrer
  2. customThe resulting suspension is deoxygenated
  3. customflushed with H2 gas for 15 min
  4. temperaturemaintained with a balloon
  5. customquantitative consumption of compound B1
  6. customThe reaction vessel is then vigorously purged with N2
  7. filtrationthe suspension is filtered through a bed of Celite and SiO2
  8. washAfter washing the insolubles with copious quantities of CH2Cl2 and EtOAc
  9. concentrationthe filtrate is concentrated in vacuo to the title compound as a mixture of four diastereomers (1.116 g, 95% crude yield, ES−=648.9)
  10. customThis material is used further without purification

Sources & evidence

ORD record
ord-4da39f1b0b0f405581a656ed3b65e395
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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