Pyridine → HCID 49848188, compound

HRID 389867Notes

Reaction equation

HRID 389867 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[CH2:10][C@H:9]2[C:13]([OH:15])=O)=[CH:4][CH:3]=1.[NH2:16][C:17]1[O:21][N:20]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O>[C:22]([C:19]1[CH:18]=[C:17]([NH:16][C:13]([C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:15])[O:21][N:20]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 67284804HCID 67284804, compound

Product 1

HCID 49848188HCID 49848188, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cold slurry of (S)-1-(4-Chloro-phenyl)-4-oxo-azetidine-2-carboxylic acid (0.2 g; 1.037 mmol) and 5-amino-3-tert-butylisoxazole (0.145 g; 1.037 mmol) in pyridine (1.258 mL; 15.555 mmol) is added phosphorous oxychloride (0.116 mL; 1.244 mmol). The mixture is stirred at 0° C. for 30 minutes and then diluted with water and extracted with ethyl acetate several times. The organics are combined and washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 348 [M+H+]

Workup

  1. extractionextracted with ethyl acetate several times
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-2e5564338fca4702b9ceb237c9145b1e
Source dataset
uspto-grants-2013_02
Patent number
US08383615B2

Reaction notes

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