Phosphorus oxychloride → HCID 58563896, compound

HRID 336206Notes

Reaction equation

HRID 336206 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O: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.C(N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O: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

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-HCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acid

Product 1

HCID 58563896HCID 58563896, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cold (0° C.) solution of morpholine-2,4-dicarboxylic acid 4-tert-butyl ester (1 g; 4.424 mmol) and 3-amino-5-t-butylisoxazole (606 mg; 4.324 mmol) and N,N-diisopropylethylamine (1.521 mL; 8.732 mmol) in anhydrous acetonitrile (12 mL) is added phosphorous oxychloride (0.39 mL; 4.424 mmol). The reaction mixture is stirred at room temperature for 18 hours. After this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution and extracted with ethyl acetate twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using ethyl acetate/Hexanes provides the title compound, m/z 354 [M+H+].

Workup

  1. customAfter this time, the reaction mixture is quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with ethyl acetate twice
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9af40c321f4242e7a7dbd0b5e5095cd6
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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