Triethylamine → HCID 13473139, compound

HRID 1248637Notes

Reaction equation

HRID 1248637 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][S:9][CH3:10])[NH2:6].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1.[O:34]=[C:35]1[NH:39][CH:38]([CH2:40][CH2:41][C:42](O)=[O:43])[CH2:37][CH2:36]1>ClCCl.CN(C)C1C=CN=CC=1>[O:43]=[C:42]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:11])[CH2:7][CH2:8][S:9][CH3:10])[CH2:41][CH2:40][CH:38]1[CH2:37][CH2:36][C:35](=[O:34])[NH:39]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 45856673-(5-Oxopyrrolidin-2-yl)propanoic acidHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 13473139HCID 13473139, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5.0 g (0.025 mol) L-methionine methyl ester hydrochloride is dissolved in 30 ml of dichloromethane. The solution is cooled to 0° C. and 4.42 ml (0.028 mol) of triethylamine is added dropwise over a ten minute period. The mixture is stirred 15 minutes, filtered, and a mixture of the following is added in a single addition: 6.32 g (0.03 mol) of dicyclohexylcarbodiimide; 200 mg (0.0016 mol) of 4-dimethylaminopyridine; 3.85 g (0.025 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 dichloromethanemethanol 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-methionine, methyl ester with a melting point of 98°-100° C.

Workup

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

Sources & evidence

ORD record
ord-d6e86b4bf7ac46e595d9767525860d6a
Source dataset
uspto-grants-1985_06
Patent number
US04525476

Reaction notes

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