Phosphorus oxychloride → HCID 58563844, compound

HRID 336177Notes

Reaction equation

HRID 336177 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][N:19]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[O:16])[NH:17][C:18]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[O:20][N:19]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 58563844HCID 58563844, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (5° C.) solution of piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (1 g; 4.362 mmol) and 3-amino-5-t-butylisoxazole (589 mg; 4.2 mmol) in anhydrous pyridine (12 mL) is added phosphorus oxychloride (0.393 mL; 4.362 mmol). The reaction mixture is stirred at room temperature for 30 minutes. The mixture is quenched with saturated NH4Cl aqueous solution and extracted with ethyl acetate 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica using methanol/methylene chloride provides the title compound, m/z 352 [M+H+].

Workup

  1. customThe mixture is quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with ethyl acetate 3 times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica

Sources & evidence

ORD record
ord-530398048fa14b6ea64664227238925f
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

Loading…