Water → HCID 10914002, compound

HRID 1393400Notes

Reaction equation

HRID 1393400 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14](=[O:29])[CH2:15][CH:16]([NH:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[C:17](=O)[CH3:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>CN(C=O)C>[CH2:6]([O:13][C:14](=[O:29])[CH2:15][C:16]1[N:20]=[C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[O:22][C:17]=1[CH3:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 10882117HCID 10882117, compound

Product 1

HCID 10914002HCID 10914002, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Phosphorous oxychloride (22 mL, 0.235 moles, 3.0 eq) was added dropwise to a solution of 3-(cyclohexanecarbonyl-amino)-4-oxo-pentanoic acid benzyl ester (26.0 g, 0.078 moles) in DMF (330 mL). The mixture was heated to 90° C. for 30 min, and then cooled to ambient temperature before diluting by slowly adding DI water (600 mL, Caution, exothermic). The mixture was cooled to ambient temperature and extracted with MTBE (3×150 mL). The combined organic phases were washed with DI water, brine (150 mL), dried over MgSO4 and concentrated to obtain 21.1 g as a brown oil. Further purification was not necessary.

Workup

  1. temperaturecooled to ambient temperature
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted with MTBE (3×150 mL)
  4. washThe combined organic phases were washed with DI water, brine (150 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto obtain 21.1 g as a brown oil
  8. customFurther purification

Sources & evidence

ORD record
ord-fdb6d0a95d044cfd8dacfb64ae6c08d1
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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