Thionyl Chloride → HCID 59370452, compound

HRID 1685373Notes

Reaction equation

HRID 1685373 reaction equation
[CH:1]([NH:4][C:5]([NH:7][C@H:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][C:10](O)=[O:11])=[O:6])([CH3:3])[CH3:2].S(Cl)(Cl)=O>C1(C)C=CC=CC=1.O>[CH:1]([N:4]1[C:10](=[O:11])[CH2:9][C@@H:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 28737755HCID 28737755, compound

Product 1

HCID 59370452HCID 59370452, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of (S)-3-{[(isopropylamino)carbonyl]amino}-3-phenylpropanoic acid from Step A (465 mg, 1.86 mmol) and thionyl chloride (0.270 mL, 3.72 mmol) in toluene (19 mL) was heated at reflux for 1 h. The reaction mixture was cooled, diluted with water (25 mL), and extracted with CH2Cl2 (3×25 mL). The combined CH2Cl2 extracts were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=233 (M+1).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with CH2Cl2 (3×25 mL)
  4. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51e50913af194f929d5df664c6ff8de3
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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