4-Methylmorpholine → HCID 22862377, compound

HRID 1734702Notes

Reaction equation

HRID 1734702 reaction equation
[C:1]([O:5][C:6]([CH:8]([NH:18][CH3:19])[C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.CN1CCOCC1.Cl.[CH3:38][O:39][C:40](=[O:47])[C@H:41]([CH2:43][CH2:44][S:45][CH3:46])[NH2:42]>CN(C)C=O.C(Cl)CCl>[C:40]([C@@H:41]([NH:42][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([CH:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[NH:18][CH3:19])[CH:10]=1)[CH2:43][CH2:44][S:45][CH3:46])([O:39][CH3:38])=[O:47]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 23368580HCID 23368580, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 22862377HCID 22862377, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step F (0.27 g) in dimethylformamide (10 mL) was added hydroxybenzotriazole (0.16 g), EDC (0.19 g), N-methylmorpholine (0.40 mL), and (S) methione methyl ester hydrochloride (0.203 mg). After stirring for 2 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. 1HNMR (300 MHz, CDCl3)δ7.70 (2H, s), 7.40 (2H, m), 6.95 (1H, d, J=7 Hz), 4.94 (1H, q, J=7 Hz), 4.45 (2H, s), 3.81 (3H, s), 2.82 (3H, d), 2.59 (2H, m), 2.30 (1H, m), 2.13 (1H, m), 2.12 (3H, s), 1.46 (9H, s).

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-61a5d8e9f3f840b594ef93f93cb04472
Source dataset
uspto-grants-1996_07
Patent number
US05534537

Reaction notes

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