1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl L-prolinate

HRID 643812

Reaction equation

HRID 643812 reaction equation
C1(C2C=CC=CC=2)C=CC(OCC2OC(C(O)=O)=CC=2)=CC=1.Cl.[C:24]([O:28][C:29](=[O:35])[C@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)([CH3:27])([CH3:26])[CH3:25].Cl.C(N=C=NCCCN(C)C)C>O1CCCC1>[C:24]([O:28][C:29]([CH:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)=[O:35])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46831535-[(4-Phenylphenoxy)methyl]furan-2-carboxylic acid2×HCID 44629909tert-Butyl D-prolinate--hydrogen chloride (1/1)

Product 1

HCID 102884tert-butyl L-prolinateYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (of Intermediate 8; 0.134 g, 0.46 mmol), D-proline tert-butyl ester hydrochloride (Bachem; 0.22 g, 1.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (Avocado; 0.18 g, 0.95 mmol), and N,N-dimethylaminopyridine (0.166 g, 1.36 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 16 h. The solvents were evaporated under reduced pressure, and water and ethyl acetate were added. The aqueous phase was extracted three times with ethyl acetate, and the combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified using a Biotage Flash 40 purification system, eluting with methylene chloride/acetone 9:1, to give 5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-D-pyrrolidine-2-carboxylic acid tert-butyl ester as a white solid (0.115 g, 56%).

Workup

  1. customThe solvents were evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialthe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified
  8. customa Biotage Flash 40 purification system
  9. washeluting with methylene chloride/acetone 9:1

Sources & evidence

ORD record
ord-4b55ed77f1a04cefaed8fcc07fbb4178
Source dataset
uspto-grants-2010_04
Patent number
US07700632B2

Linked notes

Loading…