4-Methylmorpholine → HCID 54258508, compound

HRID 892606Notes

Reaction equation

HRID 892606 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=O)=[O:9].Cl.[CH3:19][O:20][C:21](=[O:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:19][O:20][C:21](=[O:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:12](=[O:14])[C@@H:11]1[CH2:15][CH2:16][CH2:17][N:10]1[C:8](=[O:9])[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2733200methyl L-prolinate hydrochlorideHCID 28789692HCID 28789692, compound

Product 1

HCID 54258508HCID 54258508, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-proline (3.01 g) in DMF (25 ml) were added L-proline methyl ester hydrochloride (2.07 g), HOBt (2.54 g) and N-methylmorpholine (1.38 ml). The mixture was cooled to -25° C., added with DCC (2.85 g), and stirred at a temperature of -25°-0° C. for 3 hours and at room temperature for 15 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 2.56 g of N-[(2-oxo-1-pyrrolidinyl)acetyl]-L-prolyl-L-proline methyl ester.

Workup

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

Sources & evidence

ORD record
ord-6056499913aa4e9880c2b18038b2a804
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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