Tetrahydrofuran → HCID 68310374, compound

HRID 922429Notes

Reaction equation

HRID 922429 reaction equation
[CH:1]1([N:4]([CH:20]([C:22]2[CH:23]=[N:24][C:25]([O:36][CH3:37])=[C:26]([C:28]#[C:29][CH2:30][NH:31][C:32]([O:34][CH3:35])=[O:33])[CH:27]=2)[CH3:21])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.O1CCCC1>C(OCC)(=O)C.[Pd]>[CH:1]1([N:4]([CH:20]([C:22]2[CH:23]=[N:24][C:25]([O:36][CH3:37])=[C:26]([CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][CH3:35])=[O:33])[CH:27]=2)[CH3:21])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8]2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 89939690HCID 89939690, compound

Product 1

HCID 68310374HCID 68310374, compoundYield 105.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

to a solution of tert-butyl (2R)-2-({cyclopropyl[1-(6-methoxy-5-{3-[(methoxycarbonyl)-amino]prop-1-yn-1-yl}pyridin-3-yl)ethyl]amino}carbonyl)morpholin-4-carboxylate (150 mg) in ethyl acetate (2.5 mL)-tetrahydrofuran (2.5 mL) was added 10% palladium on carbon (30 mg), and the mixture was stirred under hydrogen for 45 minutes. An insoluble was filtered off, and then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by NH-silica gel column chromatography (eluent: ethyl acetate) to give tert-butyl (2R)-2-({cyclopropyl[1-(6-methoxy-5-{3-[(methoxycarbonyl)amino]propyl}pyridin-3-yl)ethyl]amino}carbonyl)morpholine-4-carboxylate [Ex(296-5)] (159 mg) as a colorless oil.

Workup

  1. filtrationAn insoluble was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by NH-silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-db01c88749694e9bb246f8fe7475f979
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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