Ethanol → HCID 50996754, compound

HRID 1026590Notes

Reaction equation

HRID 1026590 reaction equation
C(O)C.[Cl:4][C:5]1[CH:47]=[N:46][C:8]2[O:9][C:10]([CH3:45])([CH3:44])[C:11](=[O:43])[N:12]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][C@H:34]([CH3:39])[CH2:35][C:36]([OH:38])=[O:37])=[CH:23][C:22]=4[N+:40]([O-])=O)=[O:20])[CH2:15][CH2:14]3)[C:7]=2[CH:6]=1.[Cl-].[NH4+]>[Fe].O>[NH2:40][C:22]1[CH:23]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C@H:34]([CH3:39])[CH2:35][C:36]([OH:38])=[O:37])[CH:25]=[CH:26][C:21]=1[C:19]([N:16]1[CH2:17][CH2:18][CH:13]([N:12]2[C:11](=[O:43])[C:10]([CH3:45])([CH3:44])[O:9][C:8]3[N:46]=[CH:47][C:5]([Cl:4])=[CH:6][C:7]2=3)[CH2:14][CH2:15]1)=[O:20]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 68006115HCID 68006115, compound

Product 1

HCID 50996754HCID 50996754, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To an 80% aqueous ethanol solution (7.50 ml) of (3R)-3-[(4′-{[4-(7-chloro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidin-1-yl]carbonyl}3′-nitrobiphenyl-2-yl)oxy]butanoic acid (132 mg) were added at room temperature ammonium chloride (11.3 mg) and iron powder (59.0 mg), followed by stirring under heating at reflux for 1 hour. Water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford (3R)-3-[(3′-amino-4′-{[4-(7-chloro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidin-1-yl]carbonyl}biphenyl-2-yl)oxy]butanoic acid (40.5 mg).

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d249d8c718424966beec0a98af368978
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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