4-Methylmorpholine → HCID 22457732, compound

HRID 2184731Notes

Reaction equation

HRID 2184731 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][CH:6]([C:12](=[O:19])[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:7][C:8]([O:10][CH3:11])=[O:9].[C:20]([NH:23][CH2:24][CH2:25][C:26](O)=[O:27])(=[O:22])[CH3:21].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl>[C:20]([NH:23][CH2:24][CH2:25][C:26]([NH:1][CH2:2][CH2:3][S:4][CH2:5][CH:6]([C:12](=[O:19])[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:27])(=[O:22])[CH3:21]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 76406N-Acetyl-beta-alanineHCID 22457738HCID 22457738, compound

Product 1

HCID 22457732HCID 22457732, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3-[(2-aminoethylthio)methyl]-4-oxo-4-(3-pyridyl)butanoate (747 mg), 3-(acetylamino)propanoic acid (302 mg), dicyclohexylcarbodiimide (433 mg), 1-hydroxybenzotriazole (567 mg) and N-methylmorpholine (402 mg) in dichloromethane (10 mL) were stirred at room temperature overnight. The solution was concentrated and purified by flash chromatography (SiO2, chloroform:methanol=9:1) to give the title compound in 75% yield; ESMS (M+1)+353.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by flash chromatography (SiO2, chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-a1b0a35d5d6d4f77af854260057123ec
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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