Triethylamine → HCID 11348025, compound

HRID 1635067Notes

Reaction equation

HRID 1635067 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([N:7]([CH2:19][C:20](O)=[O:21])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:5][NH2:6].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C(OCC)(=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][NH:6][C:20](=[O:21])[CH2:19][N:7]1[S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54109901HCID 54109901, compound

Product 1

HCID 11348025HCID 11348025, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-2-[carboxymethyl-(4-methoxybenzenesulfonyl)-amino]propionic acid methyl ester trifluoraoetic acid salt (2.11 grams, 6.1 mmol) in methylene chloride (5 ml) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.76 grams, 9.2 mmol) and triethyamine (3.4 ml, 24.4 mmol). The resulting mixture is stirred overnight, diluted wit ethyl acetate and washed with 1N hydrochlori acid. The organic layer is dried (sodium sulfate), filtered and concentrated. The crude product is purified by silica gel chromatography (elution with ethyl acetate) to provide 1-(4-methoxybenzenesufonyl)-5-oxo-piperazine-2-carboxylic acid methyl ester.

Workup

  1. washwashed with 1N hydrochlori 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 ethyl acetate)

Sources & evidence

ORD record
ord-ae1239d3c54745669708597e11e5879b
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

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