Propanoyl chloride, 3-bromo- → HCID 54362419, compound

HRID 2051611Notes

Reaction equation

HRID 2051611 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[Br:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>[OH-].[Na+]>[Br:9][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]

Participants

4

Reactant 2

HCID 84944Propanoyl chloride, 3-bromo-HCID 145742L-Proline

Product 1

HCID 54362419HCID 54362419, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

L-proline (5.75 g.) is dissolved in N sodium hydroxide with stirring in an ice bath. To this 50 ml. of N sodium hydroxide is added followed immediately by 3-bromopropanoyl chloride (8.5 g.). The pH is about 8 and the bath is removed. After 1.5 hours an additional 2.5 ml. of 2 N sodium hydroxide is added to bring the pH to 7. The reaction mixture is extracted twice with ether, the aqueous portion is acidified with concentrated hydrochloric acid and extracted into ethyl acetate. Yield 7.7 g. The 1-(3-bromo-1-oxopropyl)-L-proline is converted with dicyclohexylamine in ethyl acetate to the dicyclohexylamine salt, m.p. 284°-286°. This salt is then converted to the free acid with 10% potassium bisulfate in ethyl acetate. This product is recrystallized from ethyl acetate:hexane and recrystallized from ethyl acetate, m.p. 83°-85°.

Workup

  1. customThe pH is about 8 and the bath is removed
  2. additionof 2 N sodium hydroxide is added
  3. extractionThe reaction mixture is extracted twice with ether
  4. extractionextracted into ethyl acetate
  5. customThis product is recrystallized from ethyl acetate
  6. customhexane and recrystallized from ethyl acetate, m.p. 83°-85°

Sources & evidence

ORD record
ord-769ce84b9ed34d988c7afa22d25c055a
Source dataset
uspto-grants-1980_01
Patent number
US04181663

Reaction notes

Loading…