4-Methylmorpholine → HCID 54195888, compound

HRID 847626Notes

Reaction equation

HRID 847626 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[CH2:12]([O:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1.CN1CCOCC1>ClCCl.C(OCC)C>[CH2:12]([O:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:24])[CH3:25])[NH:22][C:28]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 11567066O-benzyl-L-valine toluene-p-sulphonate

Product 1

HCID 54195888HCID 54195888, compoundYield 103.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.44 g (6.44 mmol) of L-valine benzyl ester p-toluenesulfonate in 100 ml of dichloromethane was cooled under N2 atmosphere to 0° C. and treated sequentially with 1.15 g (6.44 mmol) of nicotinyl chloride hydrochloride and 2.8 ml (26 mmol) of 4 -methylmorpholine. After being stirred at ambient temperature overnight, the resulting solution was diluted with 200 ml of diethyl ether, washed sequentially with water, aqueous NaHCO3, and saturated brine, dried over Na2SO4, and concentrated in vacuo to give 2.09 g (95%) of the desired compound. 1H NMR (CDCl3) δ 0.96 (d, J=7 Hz, 3H), 1.01 (d, J=7 Hz, 3H), 2.30 (m, 1H), 4.83 (dd, J=9, 5 Hz, 1H), 5.20 (AA', 2H), 6.67 (br d, 1H), 7.37 (br s, 6H), 8.11 (dd, J=8, 2 Hz, 1H), 8.74 (br, 1H), 9.01 (s, 1H).

Workup

  1. washwashed sequentially with water, aqueous NaHCO3, and saturated brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c6a4bd98d834ce5b869dd0fd39fbe56
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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