4-Methylmorpholine → HCID 9427201, compound

HRID 1734704Notes

Reaction equation

HRID 1734704 reaction equation
[C:1]([O:5][C:6](C1C=CC(C(O)=O)=C(N)C=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:19]1[C:27]2N=N[NH:24][C:23]=2[CH:22]=[CH:21][CH:20]=1.CN1CC[O:32][CH2:31]C1.Cl.[CH3:36][O:37][C:38](=[O:45])[C@H:39]([CH2:41][CH2:42][S:43][CH3:44])[NH2:40]>CN(C)C=O.C(Cl)CCl>[C:38]([C@@H:39]([NH:40][C:31](=[O:32])[C:20]1[CH:19]=[CH:27][C:23]([NH:24][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:22][CH:21]=1)[CH2:41][CH2:42][S:43][CH3:44])([O:37][CH3:36])=[O:45]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 23368594HCID 23368594, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 9427201HCID 9427201, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step A (0.5 g) in dimethylformamide (20 mL) was added hydroxybenzotriazole (0.37 g), EDC (0.51 g), N-methylmorpholine 0.8 mL), and (S) methione methyl ester hydrochloride (0.49 g). After stirring for 16 h the solution was concentrated in vacuo and the residue was partitioned with water and ethyl acetate. The ethyl acetate layer was washed with saturated sodium hydrogen carbonate, 2% potassium hydrogen sulfate and saturated sodium chloride, dried over magnesium sulfate, and concentrated in vacuo to yield the title compound.

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue was partitioned with water and ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated sodium hydrogen carbonate, 2% potassium hydrogen sulfate and saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2dab55f5fc72475881c124ba928c92b4
Source dataset
uspto-grants-1996_07
Patent number
US05534537

Reaction notes

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