4-Methylmorpholine → HCID 22907047, compound

HRID 742044Notes

Reaction equation

HRID 742044 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:13]2([C:26](O)=[O:27])[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CN1CCOCC1.Cl.[C:44]([O:48][NH2:49])([CH3:47])([CH3:46])[CH3:45].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.O>[C:44]([O:48][NH:49][C:26]([C:13]1([N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14]1)=[O:27])([CH3:47])([CH3:46])[CH3:45]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 229072304-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carboxy]piperidine

Product 1

HCID 22907047HCID 22907047, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carboxy]-piperidine (850.0 mg, 1.64 mmol) in methylene chloride (100 mL) containing N-methylmorpholine (0.6 ml, 5.48 mmol) and O-t-butylhydroxyl amine hydrochloride (620.0 mg, 4.94 mmol) is added N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (1.1 g, 5.74 mmol). The reaction mixture is stirred overnight at room temperature. The mixture is diluted with water and extracted with methylene chloride. The combined organic extracts are dried (Na2SO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (ethyl acetate) to provide 4-[N-t-butyloxy-carbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-piperidine.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. customthe solvent is evaporated
  4. customThe crude product is purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bd342527dbab4b268c90f12665dc57c5
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

Loading…