1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 21997034, compound

HRID 1978222Notes

Reaction equation

HRID 1978222 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]([CH2:17][CH2:18][CH2:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:14]([OH:16])=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH2:32](NO)[C:33]1C=CC=C[CH:34]=1.Cl.C[N:43](C)CCCN=C=NCC.[O:53]1[CH2:57][CH2:56][CH2:55][CH2:54]1.O>C(OCC)(=O)C>[CH2:57]([O:53][NH:43][C:14](=[O:16])[CH:13]([CH2:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH2:17][CH2:18][CH2:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:21])=[O:22])[C:56]1[CH:34]=[CH:33][CH:32]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 21881883Oxolane--water (1/1)HCID 21997010HCID 21997010, compound

Product 1

HCID 21997034HCID 21997034, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[(4-methoxybenzenesulfonyl)methyl]-5-(4-methoxybenzenesulfonyl)-pentanoic acid (0.5 g, 1.1 mmol), benzylhydroxylamine hydrochloride (0.21 g, 1.3 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.42 g, 2.2 mmol), and tetrahydrofuran/water (1/1, 10 mL) is stirred at ambient temperature overnight. The mixture is transferred to ethyl acetate which is extracted with aqueous 10% hydrochloric acid, distilled water, aqueous sodium bicarbonate, and brine. The organic phase is concentrated in vacuo to yield the title compound as a white solid.

Workup

  1. extractionis extracted with aqueous 10% hydrochloric acid
  2. distillationdistilled water, aqueous sodium bicarbonate, and brine
  3. concentrationThe organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-218483b067ba4c55b61a4b5f257ed9e2
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

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