Sulfuric acid magnesium salt (1:1) → HCID 86666276, compound

HRID 1026251Notes

Reaction equation

HRID 1026251 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[C:6]([N+:12]([O-])=O)[CH:5]=1)[CH3:2].[NH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])=[CH:18][C:17]=1[F:34].S([O-])([O-])(=O)=O.[Mg+2]>C(O)C>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]2[C:6]([CH:5]=1)=[N:12][N:15]([C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH3:23])=[CH:18][C:17]=1[F:34])[CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 84665874HCID 84665874, compoundHCID 86666275HCID 86666275, compound

Product 1

HCID 86666276HCID 86666276, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-ethoxy-2-nitrobenzaldehyde (5.20 g), tert-butyl [(1S)-2-(4-amino-3-fluorophenoxy)-1-methylethyl]carbamate (7.58 g), magnesium sulfate (3.21 g) and ethanol (60 mL) was stirred under reflux overnight. The reaction mixture was concentrated under reduced pressure, triethyl phosphite (13.7 ml) was added to the residue, and the mixture was stirred at 130° C. for 3 hr. The reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a yellow solid (6.53 g).

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure, triethyl phosphite (13.7 ml)
  3. additionwas added to the residue
  4. stirringthe mixture was stirred at 130° C. for 3 hr
  5. customThe reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b9ff75fb416348e4a97d50b14e340053
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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