4-Methylmorpholine → N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanamide

HRID 2209683Notes

Reaction equation

HRID 2209683 reaction equation
[Li+].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:14]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:15]([O-])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.[C:51]([O:55][NH2:56])([CH3:54])([CH3:53])[CH3:52].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl>[C:51]([O:55][NH:56][C:15](=[O:16])[C@H:14]([N:13]([S:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])([CH3:54])([CH3:53])[CH3:52]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 700596162(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanoic acid lithium salt

Product 1

HCID 10625382N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanoic acid lithium salt (4.42 g, 10.18 mmol) in methylene chloride (100 mL) containing N-methylmorpholine (6.73 mL, 61.06 mmol), 1-hydroxybenzotriazole monohydrate (1.64 g, 10.687 mmol) and O-t-butylhydroxyl amine hydrochloride (1.41 g, 11.20 mmol) is added N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (3.90 g, 20.36 mmol) at 0° C. The reaction mixture is allowed to warm to room temperature and stirring is continued overnight. The mixture is diluted with methylene chloride, washed with saturated sodium bicarbonate, then with brine, dried (Na2SO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (10:1:0.5 ethyl acetate/methanol/ammonium hydroxide) to provide N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanamide.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialwith brine, dried (Na2SO4)
  3. customthe solvent is evaporated
  4. customThe crude product is purified by silica gel chromatography (10:1:0.5 ethyl acetate/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-cd2668f60d724b73a9dc7b4d51760cc7
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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