4-Methylmorpholine → HCID 22862377, compound

HRID 1901589Notes

Reaction equation

HRID 1901589 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) δ 7.70 (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-cbf3fc11b00943888227a21b177e2649
Source dataset
uspto-grants-1996_11
Patent number
US05578629

Reaction notes

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