Potassium Carbonate → HCID 67612103, compound

HRID 1385816Notes

Reaction equation

HRID 1385816 reaction equation
C1(C)C=CC(S(NC(CC)CO[S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])(=O)=O)=CC=1.Br.Br.Br.[CH2:30]([CH:32]1[CH2:40][NH:39][CH2:38][CH:37]([CH2:41][CH3:42])NCCN1)[CH3:31].C(=O)([O-])[O-].[K+].[K+]>>[C:20]1([CH3:23])[CH:19]=[CH:18][C:17]([S:14]([CH2:42][CH2:41][CH2:37][CH2:38][NH:39][CH2:40][CH2:32][CH2:30][CH3:31])(=[O:15])=[O:16])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 86757164HCID 86757164, compound

Product 1

HCID 67612103HCID 67612103, compound

Procedure

1.1.7 2,6-Diethyl-1,4,7-triazacyclononane trihydrobromide 2-(p-toluenesulfonylamino)-1-(p-toluenesulfonyloxy) butane (1.1.8) and ammonium hydroxide were reacted to form 2-(p-toluenesulfonamino)-1-aminobutane (1.1.9). This was reacted with 2-(p-toluenesulfonylamino)-1-(p-toluenesulfonyloxy)butane (1.1.8) and potassium carbonate. The 3,7 bis(p-toluenesulfonylamino)-5-azanonane (1.1.10) product was purified by chromatography and reacted with p-toluenesulfonyl chloride to obtain the corresponding tri-p-toluenesulfonyl compound 3,7 bis(p-toluenesulfonylamino)-5-(p-toluenesulfonyl-5-azanonane (1.1.11). This was purified by chromatography and reacted with 2.2 equivalents of sodium amide in DMF and then with 1,2-di(p-toluenesulfonyloxy)ethane (1.1.1 2). The 2,6-diethyl-1,4,7-tris(p-toluenesulfonyl) triazacyclononane (1.1.13) that was obtained following purification was heated in a solution of HBr in acetic acid to remove the p-toluenesulfonyl groups and form the titled compound (1.1.7)

Workup

  1. customThe 3,7 bis(p-toluenesulfonylamino)-5-azanonane (1.1.10) product was purified by chromatography
  2. customreacted with p-toluenesulfonyl chloride

Sources & evidence

ORD record
ord-776da3e69eaf44d0b2d2ef700cfdb423
Source dataset
uspto-grants-2001_07
Patent number
US06264966B1

Reaction notes

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