4-Methylmorpholine → HCID 54370671, compound

HRID 892604Notes

Reaction equation

HRID 892604 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.CN1CCOCC1.[O:18]=[C:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][C:25](O)=[O:26].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:25](=[O:26])[CH2:24][N:20]1[CH2:21][CH2:22][CH2:23][C:19]1=[O:18]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2733200methyl L-prolinate hydrochlorideHCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acid

Product 1

HCID 54370671HCID 54370671, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of L-proline methyl ester hydrochloride (8.28 g) in DMF (100 ml) were added N-methylmorpholine (5.50 ml), 2-oxo-1-pyrrolidine acetic acid (7.15 g) and HOBt (10.12 g) under ice-cooling. The mixture was cooled to -25° C., added with DCC (10.32 g), and stirred at room temperature for 16 hours. The precipitated dicyclohexylurea was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 12.94 g of N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-proline methyl ester.

Workup

  1. temperaturecooling
  2. filtrationThe precipitated dicyclohexylurea was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-293f519766d84f558a0b421eafb5fb2b
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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