Triethylamine → HCID 70017736, compound

HRID 1940032Notes

Reaction equation

HRID 1940032 reaction equation
[Na+:1].C(NC([N:12]1[CH2:18][CH2:17][C@@H:16]2[C@H:13]1[C:14](=O)[N:15]2[S:19]([O-:22])(=[O:21])=[O:20])=O)C1C=CC=CC=1.C(N(CC)CC)C.[C:31](Cl)(=[O:40])[CH:32]=[CH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[Na+:1].[C:34]1(/[CH:33]=[CH:32]/[C:31]([C@:13]23[CH2:14][N:15]([S:19]([O-:22])(=[O:20])=[O:21])[C@@H:16]2[CH2:17][CH2:18][NH:12]3)=[O:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 70017732HCID 70017732, compound

Product 1

HCID 70017736HCID 70017736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S,5R)-2,6-Diazabicyclo[3.2.0]heptan-7-one (Example 2) (500 mg, 4.5 mmol) were suspended in 50 ml of dichloromethane. 0.75 ml (5.4 mmol) of triethylamine and subsequently 890 mg (5.4 mmol) of cinnamoyl chloride were added dropwise thereto while cooling with ice and the mixture was left to stir for 30 minutes while cooling and for 3.5 hours at room temperature. Thereafter, it was extracted once each time with saturated aqueous sodium carbonate solution, 2% aqueous citric acid solution, water and saturated aqueous sodium chloride solution. The combined organic phases were dried over magnesium sulphate and concentrated. Purification was effected by flash chromatography over silica gel with ethyl acetate. Yield: 560 mg (52%).

Workup

  1. temperaturewhile cooling with ice
  2. waitthe mixture was left
  3. extractionThereafter, it was extracted once each time with saturated aqueous sodium carbonate solution, 2% aqueous citric acid solution, water and saturated aqueous sodium chloride solution
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-6c4d7bb5a09c48edb77bf6050283fff2
Source dataset
uspto-grants-1997_12
Patent number
US05698577

Reaction notes

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