Potassium Carbonate → alpha-[3-Chloro-4-(3-hydroxypyrrolidino)-phenyl]-propionic acid

HRID 1578398Notes

Reaction equation

HRID 1578398 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[Cl:13].Cl[CH2:15][CH:16]([OH:20])[CH2:17][CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:13][C:3]1[CH:4]=[C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[N:1]1[CH2:18][CH2:17][CH:16]([OH:20])[CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170211,4-Dichloro-2-butanolHCID 130652322-(4-Amino-3-chlorophenyl)propanoic acid

Product 1

HCID 20334055alpha-[3-Chloro-4-(3-hydroxypyrrolidino)-phenyl]-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2.0 g of α-(4-amino-3-chlorophenyl)propionic acid in 20 ml of ethanol, 1.4 g of 1,4-dichloro-2-butanol are added, followed by 4 g of potassium carbonate while stirring. The mixture is stirred for 4 hours at the steam cone and evaporated under reduced pressure. The residue is taken up in water, the solution acidified with N hydrochloric acid to a pH of 5.5 and extracted with diethyl ether. The extract is dried, filtered and evaporated, to yield the α-[3-chloro-4-(3-hydroxypyrrolidino)-phenyl]-propionic acid of the formula ##SPC9##

Workup

  1. stirringThe mixture is stirred for 4 hours at the steam cone
  2. customevaporated under reduced pressure
  3. extractionextracted with diethyl ether
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-28e0374b0eb141b7aad93cf649ffa2f0
Source dataset
uspto-grants-1976_02
Patent number
US03936467

Reaction notes

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