Acryloyl chloride → HCID 67103285, compound

HRID 2079582Notes

Reaction equation

HRID 2079582 reaction equation
[CH:1]1([NH:7][CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH:1]1([N:7]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[C:17](=[O:20])[CH:18]=[CH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 13140Acryloyl chlorideHCID 67103142HCID 67103142, compound

Product 1

HCID 67103285HCID 67103285, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of the oil isolated in Step E (313 mg, 1.4 mmol) in methylene chloride (10 mL) and saturated aqueous sodium bicarbonate solution (10 m) at 0° C. was added acryloyl chloride (115 μL, 1.4 mmol). The resulting mixture was stirred for 1 h and then was extracted with methylene chloride. The solution was concentrated, the resulting residue was dissolved in MeOH (3 mL) and aqueous LiOH solution (1N, 1 mL). The mixture was then stirred at room temperature for 30 minutes. The solution was acidified with 1N HCl and then extracted with methylene chloride. The solution was dried over sodium sulfate and concentrated to yield an oil.

Workup

  1. extractionwas extracted with methylene chloride
  2. concentrationThe solution was concentrated
  3. dissolutionthe resulting residue was dissolved in MeOH (3 mL)
  4. stirringThe mixture was then stirred at room temperature for 30 minutes
  5. extractionextracted with methylene chloride
  6. dry with materialThe solution was dried over sodium sulfate
  7. concentrationconcentrated
  8. customto yield an oil

Sources & evidence

ORD record
ord-cf0abcb426ef4b1594f22a438be9ba51
Source dataset
uspto-grants-2011_04
Patent number
US07932261B2

Reaction notes

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