Triethylamine → HCID 13473143, compound

HRID 1248638Notes

Reaction equation

HRID 1248638 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH2:7])[CH3:3].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1.[O:32]=[C:33]1[NH:37][CH:36]([CH2:38][CH2:39][C:40](O)=[O:41])[CH2:35][CH2:34]1>ClCCl.CN(C)C1C=CN=CC=1>[O:41]=[C:40]([NH:7][C@H:6]([C:5]([O:4][CH2:2][CH3:3])=[O:9])[CH3:8])[CH2:39][CH2:38][CH:36]1[CH2:35][CH2:34][C:33](=[O:32])[NH:37]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 45856673-(5-Oxopyrrolidin-2-yl)propanoic acid

Product 1

HCID 13473143HCID 13473143, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5.0 g (0.033 mol) L-alanine ethyl ester hydrochloride is dissolved in 30 ml of dichloromethane. The solution is cooled to 0° C. and 5.42 ml (0.039 mol) of triethylamine is added dropwise over a ten minute period. The mixture is stirred 15 minutes, filtered, concentrated, and diluted with 60 ml of dichloromethane. A mixture of the following is added in a single addition: 4.84 g (0.025 mol) of dicyclohexylcarbodiimide; 200 mg (0.0016 mol) of 4-dimethylaminopyridine; 3.08 g (0.02 mol) of 5-oxo-2-pyrrolidinepropanoic acid. The reaction is allowed to warm to room temperature and stirred for 24 hours. The solids are removed by filtration and are washed with 15 ml of 0° C. dichloromethane. The filtrate is concentrated at reduced pressure to an oil. The oil is chromatographed over silica gel using 19:1 dichloromethane-methanol for elution. Concentration at reduced pressure followed by heating at 0.1 mm pressure and 60° C. yields crystalline analytically pure N-[1-oxo-3-(5-oxo-2-pyrrolidinyl)propyl]-L-alanine, ethyl ester with a melting point of 88°-90° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additiondiluted with 60 ml of dichloromethane
  4. additionA mixture of the following
  5. additionis added in a single addition
  6. temperatureto warm to room temperature
  7. stirringstirred for 24 hours
  8. customThe solids are removed by filtration
  9. washare washed with 15 ml of 0° C. dichloromethane
  10. concentrationThe filtrate is concentrated at reduced pressure to an oil
  11. customThe oil is chromatographed over silica gel using 19:1 dichloromethane-methanol for elution
  12. concentrationConcentration at reduced pressure
  13. temperatureby heating at 0.1 mm pressure and 60° C.

Sources & evidence

ORD record
ord-ab7a13686d514d5ba7c248115934471e
Source dataset
uspto-grants-1985_06
Patent number
US04525476

Reaction notes

Loading…