HCID 86594308, compound → HCID 68459742, compound

HRID 751176Notes

Reaction equation

HRID 751176 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[CH2:15][C@@H:14]3[C@H:16]([N:19]=[N+]=[N-])[CH2:17][CH2:18][N:13]3[C:12]2=[O:22])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>CO.O=[Pt]=O>[NH2:19][C@H:16]1[CH:14]2[N:13]([C:12](=[O:22])[N:11]([C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[C:9]=3[CH3:10])[CH2:15]2)[CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 86594308HCID 86594308, compound

Product 1

HCID 68459742HCID 68459742, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent2×

Procedure

A solution of compound 90B (20.5 mg, 0.06 mmol) in dry MeOH (1.0 mL) was treated with PtO2 (5.5 mg) and hydrogenated (balloon) at rt for 1.0 h. The reaction mixture was diluted with MeOH (1.0 mL) and filtered through a syringe filter, washing the syringe filter well with MeOH (3×1.0 mL). The clear filtrate was concentrated under reduced pressure and the residue was chromatographed (silica gel; CH2Cl2/CH3OH gradient) to yield the title compound (11.9 mg, 68.2%) as a white solid. HPLC: 100% at 1.38 min (retention time) (Conditions: YMC S-5 C-18 (4.6×50 mm), eluting with 0-100% B, 4 min gradient. (A=90% H2O—10% CH3CN—0.1% TFA and B=10% H2O—90% CH3CN—0.1% TFA); Flow rate at 4 mL/min. UV detection at 220 nm. Chiral HPLC: retention time=18.98 min (99.6%); Conditions: OD (4.6×250 mm); Eluted with 20% isopropanol in heptane for 30 min at 1 mL/min. MS (ES+): m/z 291 [M+H]+.

Workup

  1. filtrationfiltered through a syringe
  2. filtrationfilter
  3. washwashing the syringe
  4. filtrationfilter well with MeOH (3×1.0 mL)
  5. concentrationThe clear filtrate was concentrated under reduced pressure
  6. customthe residue was chromatographed (silica gel; CH2Cl2/CH3OH gradient)

Sources & evidence

ORD record
ord-f387b5db2da64e28856e3789439bda6e
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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