1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 18413944, compound

HRID 991456Notes

Reaction equation

HRID 991456 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Si]([O:33][NH2:34])(C(C)(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:34][OH:33])=[O:22])(=[O:16])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 18413947HCID 18413947, compound

Product 1

HCID 18413944HCID 18413944, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Example 63 (190 mg) was added O-(tert-butyldimethylsilyl)-hydroxylamine (81 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (96 mg). After stirring overnight at room temperature ethyl acetate (100 mL) was added and the organic layer was washed with water (2×25 ml), saturated NaHCO3 (2×25 ml) and water (25 ml), dried over MgSO4, filtered and evaporated. The colourless oil was dissolved in dichloromethane (20 ml) and treated with 1.0 M HCl solution in ether (1.5 ml). Filtration afforded the title compound as a white solid (100 mg, 50%).

Workup

  1. additionwas added
  2. washthe organic layer was washed with water (2×25 ml), saturated NaHCO3 (2×25 ml) and water (25 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe colourless oil was dissolved in dichloromethane (20 ml)
  7. additiontreated with 1.0 M HCl solution in ether (1.5 ml)
  8. filtrationFiltration

Sources & evidence

ORD record
ord-4ab81891ce7945a3a46348e68a0f2d54
Source dataset
uspto-grants-2002_10
Patent number
US06465468B1

Reaction notes

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