Triethylamine → HCID 44544858, compound

HRID 391254Notes

Reaction equation

HRID 391254 reaction equation
P(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([OH:15])=[O:14].[Br:16]Br.[O:18]=[C:19]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[C@H:20](O)[CH3:21].C(N(CC)CC)C.[OH-].[Na+]>O.C1(C)C=CC=CC=1>[Br:16][CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[Cl:5])[C:13]([O:15][C@H:20]([CH3:21])[C:19](=[O:18])[N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:14]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 17124o-Chlorophenylacetic acidHCID 24408BromineHCID 24614Phosphorus tribromideHCID 11194401Pyrrolidine, 1-[(2R)-2-hydroxy-1-oxopropyl]- (9CI)

Product 1

HCID 44544858HCID 44544858, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To phosphorus tribromide (28 g, 103.4 mmol), 2-chlorophenylacetic acid (44 g, 257.9 mmol) was added. The mixture was stirred at 50° C. for 1 hour. After stirring, bromine (66 g, 413.0 mmol) was added thereto at the same temperature for reaction overnight. After the reaction, toluene (200 mL) and (2R)-1-oxo-1-pyrrolidinylpropane-2-ol (40.6 g, 283.6 mmol) were added thereto at the same temperature. Subsequently, triethylamine (34 g, 336.0 mmol) was added thereto to carry out reaction for 2 hours. After the reaction, water was added thereto. After the mixture was neutralized with a 30% sodium hydroxide aqueous solution, the organic layer was separated from the water layer and the water layer was disposed of. The obtained organic layer was washed with water, and the water layer was separated and disposed of. The organic layer was concentrated under reduced pressure to obtain 83.1 g of the target compound (221.8 mmol, 86%).

Workup

  1. stirringAfter stirring
  2. customat the same temperature for reaction overnight
  3. additionwere added
  4. customreaction for 2 hours
  5. additionwas added
  6. customthe organic layer was separated from the water layer
  7. washThe obtained organic layer was washed with water
  8. customthe water layer was separated
  9. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb3f5046be184fe1897458afbad647d5
Source dataset
uspto-grants-2013_02
Patent number
US08383833B2

Reaction notes

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