Tetrahydrofuran → Benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-formylquinolin-3-yl)carbamate

HRID 924388Notes

Reaction equation

HRID 924388 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21][C:22]([C:24]2[C:33]([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:32][C:31]3[C:26](=[CH:27][C:28]([CH:45]=C)=[CH:29][CH:30]=3)[N:25]=2)=[O:23])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[O:50]CC1.I([O-])(=O)(=O)=O.[Na+]>O.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21][C:22]([C:24]2[C:33]([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:32][C:31]3[C:26](=[CH:27][C:28]([CH:45]=[O:50])=[CH:29][CH:30]=3)[N:25]=2)=[O:23])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 86726869Benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-vinylquinolin-3-yl)carbamate

Product 1

HCID 86726870Benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-formylquinolin-3-yl)carbamateYield 61%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Benzyl (2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-vinylquinolin-3-yl)carbamate (520 mg, 0.84 mmol) was mixed with THF (20 mL), 0.25 M osmium tetroxide in water (1.0 mL, 0.3 mmol) and sodium metaperiodate (840 mg, 3.9 mmol) in water (2 mL). The reaction mixture was stirred at 70° C. for 2 h, then allowed to cool. After cooling, the mixture was filtered through a diatomaceous earth plug, which was rinsed with fresh THF. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column eluting with EtOAc in hexanes (0-100%) to give the sub-title compound (320 mg, 61%) as yellow powder. LCMS calc. for C34H37N6O6 (M+H)+: m/z=625.2. Found: 625.1.

Workup

  1. temperatureto cool
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through a diatomaceous earth plug, which
  4. washwas rinsed with fresh THF
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column
  7. washeluting with EtOAc in hexanes (0-100%)

Sources & evidence

ORD record
ord-40ac9bfdde3b47d2a05a71281bd6b0ad
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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