4-Methylmorpholine → HCID 9954224, compound

HRID 2297717Notes

Reaction equation

HRID 2297717 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.[C:37]([S:40][CH2:41][CH2:42][N:43]([CH2:52][CH2:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1)[C:44](=[O:51])[NH:45][C@@H:46]([CH3:50])[C:47]([OH:49])=O)(=[O:39])[CH3:38]>C(Cl)Cl>[C:37]([S:40][CH2:41][CH2:42][N:43]([CH2:52][CH2:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1)[C:44](=[O:51])[NH:45][C@@H:46]([CH3:50])[C:47]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:49])(=[O:39])[CH3:38]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59923449HCID 59923449, compound

Product 1

HCID 9954224HCID 9954224, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In anhydrous methylene chloride (5 ml) are dissolved (2S)-2-[3-[2-(acetylthio)ethyl]-3-(2-cyclohexylethyl)ureido]propionic acid (Compound No. 7-1, 826 mg), N-methylpiperazine (0.27 ml) and 1-hydroxybenzotriazole (357 mg) under a nitrogen atmosphere. To the solution are added N-methylmorpholine (0.29 ml) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (506 mg) successively under ice cooling, and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure, a 5% aqueous sodium hydiogencarbonate solution (30 ml) is added to the resulting oily matter, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 801 mg (78%) of the titled compound (Compound No. 13-1).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additiona 5% aqueous sodium hydiogencarbonate solution (30 ml) is added to the resulting oily matter
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe organic layer is washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-333c0deddd024e3a9863084e91f9f8a6
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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