Triethylamine → HCID 44544857, compound

HRID 391255Notes

Reaction equation

HRID 391255 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([OH:15])=[O:14].S(Cl)([Cl:19])(=O)=O.[O:21]=[C:22]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C@H:23](O)[CH3:24].C(N(CC)CC)C>O.C1(C)C=CC=CC=1>[Cl:19][CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[Cl:5])[C:13]([O:15][C@H:23]([CH3:24])[C:22](=[O:21])[N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:14]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 17124o-Chlorophenylacetic acidHCID 24386Thionyl ChlorideHCID 24648Sulfuryl chlorideHCID 11194401Pyrrolidine, 1-[(2R)-2-hydroxy-1-oxopropyl]- (9CI)

Product 1

HCID 44544857HCID 44544857, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To thionyl chloride (7.7 g, 64.7 mmol), 2-chlorophenylacetic acid (10 g, 58.6 mmol) was added. The mixture was stirred at 50° C. for 3 hours. After stirring, sulfuryl chloride (12.7 g, 93.8 mmol) was added thereto at the same temperature for reaction overnight. After the reaction, toluene (45 mL) was added and (2R)-1-oxo-1-pyrrolidinylpropane-2-ol (9.2 g, 64.5 mmol) was added thereto at the same temperature. Subsequently, triethylamine (7.7 g, 93.8 mmol) was added to carry out reaction for 2 hours. After the reaction, water was added thereto and the water layer was disposed of. The obtained organic layer was washed with water, and the water layer was disposed of. The organic layer was concentrated under reduced pressure to obtain 19 g of the concentrate of the target compound.

Workup

  1. stirringAfter stirring
  2. customat the same temperature for reaction overnight
  3. additionwas added
  4. customreaction for 2 hours
  5. additionwas added
  6. washThe obtained organic layer was washed with water
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customto obtain 19 g of the
  9. concentrationconcentrate of the target compound

Sources & evidence

ORD record
ord-7302bdd5c36e44e8b1d26a44d29f3500
Source dataset
uspto-grants-2013_02
Patent number
US08383833B2

Reaction notes

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