Triethylamine → HCID 18675466, compound

HRID 1635068Notes

Reaction equation

HRID 1635068 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][C:16](=[O:18])[NH:15][CH2:14][CH:13]2[C:19](O)=[O:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][NH2:30])=[CH:24][CH:23]=1.Cl.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:28]([O:29][NH:30][C:19]([CH:13]1[CH2:14][NH:15][C:16](=[O:18])[CH2:17][N:12]1[S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])=[O:20])[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18675471HCID 18675471, compound

Product 1

HCID 18675466HCID 18675466, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-methoxybenzenesulfonyl)-5-oxo-piperazine-2-carboxylic acid (166 mg, 0.53 mmol) in methylene chloride (5 ml) is added 0-benzyl hydroxylamine hydrochloride (255 mg, 1.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (153 mg, 0.8 mmol) and triethylamine (370 μL 2.65 mmol). The resulting mixture is stirred overnight, diluted with ethyl acetate and washed with 1N hydrocloric acid. The organic layer is dried (sodium sulfate), filtered and concentrated. The crude product is purified by silica gel chromatography (elution with 5% methanol in methylene chloride) to provide N-(benzyloxy)-1-(4-methoxybenzenesulfonyl)-5-oxo-piperazine-2-carboxamide.

Workup

  1. washwashed with 1N hydrocloric acid
  2. dry with materialThe organic layer is dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel chromatography (elution with 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-d07d67ae9b5d4a978e0a8fd436410f11
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

Loading…