HCID 69266135, compound → HCID 69266352, compound

HRID 2377024Notes

Reaction equation

HRID 2377024 reaction equation
C([O:8][CH2:9][C@:10]12[S:18](=[O:20])(=[O:19])[N:17]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=3)[CH2:16][C@H:15]1[C@@H:14]1[CH2:33][C@H:11]2[CH:12]=[CH:13]1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.CO.[Pd]>[OH:8][CH2:9][C@:10]12[S:18](=[O:20])(=[O:19])[N:17]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:31])([F:32])[F:30])[CH:22]=3)[CH2:16][C@H:15]1[C@@H:14]1[CH2:33][C@H:11]2[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 69266135HCID 69266135, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69266352HCID 69266352, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution-suspension of Example 30 (50 mg, 0.11 mmol) and Degussa-type Pd/C (10 mg; 20 wt %) in 4 mL EtOAc/MeOH (2:1) was stirred under 1 atmosphere of hydrogen at ambient temp for 5 hrs. The reaction vessel was then purged with N2 to give a black suspension that was then filtered. The resulting colorless filtrate was concentrated in vacuo to give 35 mg of a mixture of starting material and product in a 2:1 ratio. The mixture was dissolved in CH2Cl2, loaded onto a preparative TLC plate, and eluted with 30% acetone/heptane to afford 15 mg Example 32 (36% yield) as a colorless film. HPLC: 98% at 3.015 min (retention time) (YMC ODS-A column 4.6×50 mm eluting with 10-90% aqueous MeOH over 4 min containing 0.1% H3PO4, 4 mL/min, monitoring at 220 nm); and MS (ES): m/z 445.11 [M−H+ OAc]−.

Workup

  1. customThe reaction vessel was then purged with N2
  2. customto give a black suspension that
  3. filtrationwas then filtered
  4. concentrationThe resulting colorless filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-64ceef69d71349d6aa3786dcd7753d09
Source dataset
uspto-grants-2008_12
Patent number
US07468439B2

Reaction notes

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