4-Methylmorpholine → HCID 22856310, compound

HRID 1720595Notes

Reaction equation

HRID 1720595 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:14]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:28])[CH2:24][N:25]([CH3:27])[CH3:26])[C:15](O)=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[C:55]([O:59][NH2:60])([CH3:58])([CH3:57])[CH3:56].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.CN(C)C=O>[C:55]([O:59][NH:60][C:15](=[O:16])[C@H:14]([N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=1)(=[O:11])=[O:12])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:28])[CH2:24][N:25]([CH3:27])[CH3:26])([CH3:58])([CH3:57])[CH3:56]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 70060004HCID 70060004, compound

Product 1

HCID 22856310HCID 22856310, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-[(N,N-dimethylglycyl)amino] hexanoic acid hydrochloride (4.12 g, 7.82 mmol) in methylene chloride (78 mL) and dimethylformamide (5 mL) is added 1-hydroxybenzotriazole monohydrate (1.26 g, 8.21 mmol), N-methylmorpholine (2.58 ml, 23.45 mmol), and O-t-butylhydroxylamine hydrochloride (1.08 g, 8.60 mmol). The reaction is cooled to 0° C., and N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (3.0 g, 15.64 mmol) is added. The reaction mixture is warmed to room temperature and stirred overnight. The mixture is then diluted with methylene chloride and washed with saturated aqueous sodium bicarbonate, and then with brine. The organic layer is dried (Na2SO4), filtered, and and the solvent is evaporated. The crude product is purified by silica gel chromatography (10/0.5/0.5 ethyl acetate/methanol/ammonium hydroxide ) to provide N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-[(N,N-dimethylglycyl)amino] hexanamide.

Workup

  1. temperatureThe reaction mixture is warmed to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe crude product is purified by silica gel chromatography (10/0.5/0.5 ethyl acetate/methanol/ammonium hydroxide )

Sources & evidence

ORD record
ord-60285240248b47f3a75dba3a2ab574ad
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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