Potassium Carbonate → HCID 12813366, compound

HRID 262547Notes

Reaction equation

HRID 262547 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[CH2:10][CH2:11][C:12](Cl)=[O:13].[C:15]([OH:23])(=[S:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>[OH-].[Na+].O>[C:15]([S:22][CH2:10][CH2:11][C:12]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:13])(=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 145742L-ProlineHCID 178526132HCID 178526132, compound

Product 1

HCID 12813366HCID 12813366, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

L-Proline (5.75 g.) is dissolved in normal sodium hydroxide (50 ml.) and the solution is chilled in an ice bath. 3-Bromopropionyl chloride (8.5 g.) and 2 N sodium hydroxide (27 ml.) are added and the mixture is stirred for 10 minutes in the ice bath and three hours at room temperature. A suspension of thiobenzoic acid (7.5 g.) and potassium carbonate (4.5 g.) in water (50 ml.) is added and the mixture is stirred for 18 hours at room temperature. After acidification with concentrated hydrochloric acid, the aqueous phase is extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate and concentrated to dryness in vacuo to obtain 1-(3-benzoylthiopropanoyl)-L-proline, yield 7.1 g., m.p. 101°-102° (ethyl acetate-hexane).

Workup

  1. temperaturethe solution is chilled in an ice bath
  2. additionis added
  3. extractionAfter acidification with concentrated hydrochloric acid, the aqueous phase is extracted twice with ethyl acetate
  4. dry with materialThe organic layers are dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b00f4d6759ce488ba2dd0c3a7f9425b9
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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