1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 9924157, compound

HRID 990698Notes

Reaction equation

HRID 990698 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH2:8][N:9]([CH3:20])[C:10]([CH2:12][CH:13]([CH:17]([CH3:19])[CH3:18])[C:14](O)=[O:15])=[O:11])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[Si]([O:42][NH2:43])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.O1CCCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][CH2:8][N:9]([CH3:20])[C:10](=[O:11])[CH2:12][CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([NH:43][OH:42])=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 70106451HCID 70106451, compound

Product 1

HCID 9924157HCID 9924157, compoundYield 7.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Intermediate 25 (0.31 g) in dichloromethane (15 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.21 g) and O-tert-butyldimethylsilylhydroxylamine (0.17 g) and the mixture was stirred for 18 h, then washed with water (40 ml), and the aqueous extracted with dichloromethane (20 ml). The combined organic extracts were dried over magnesium sulphate (1 g) and evaporated to give a yellow gum. This was taken up in tetrahydrofuran (20 ml), cooled to 0° C. and tetrabutylammonium fluoride (1M, 1.08 ml) added and the reaction stirred for 8 min, before acetic acid (2 drops) was added. The solvent was removed in vacua, water (10 ml) was added, and the slurry extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with brine (30 ml), dried over magnesium sulphate (0.5 g) and the solvent removed in vacua. Purification by flash chromatography (silica, eluent 5% methanol/dichloromethane) yielded the title compound as a gummy solid (0.023g).

Workup

  1. washwashed with water (40 ml)
  2. extractionthe aqueous extracted with dichloromethane (20 ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate (1 g)
  4. customevaporated
  5. customto give a yellow gum
  6. additionwas added
  7. customThe solvent was removed in vacua, water (10 ml)
  8. additionwas added
  9. extractionthe slurry extracted with ethyl acetate (2×25 ml)
  10. washThe combined organic extracts were washed with brine (30 ml)
  11. dry with materialdried over magnesium sulphate (0.5 g)
  12. customthe solvent removed in vacua
  13. customPurification by flash chromatography (silica, eluent 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-12770c3f8468462891b910eb416ec895
Source dataset
uspto-grants-2002_10
Patent number
US06462042B1

Reaction notes

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