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1-Azido-3-iodopropane → Spermine

HRID 968183
Notes
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Reaction equation

HRID 968183 reaction equation
C([CH:8]([CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH2:34][NH2:35])[N:9](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)(OC(C)(C)C)=O.N(CCCI)=[N+]=[N-]>[Pd]>[NH2:35][CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24][CH2:8][NH2:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 109108231-Azido-3-iodopropaneHCID 22610912TriBoc-Spermine

Product 1

HCID 1103Spermine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Monoquaternary spermine containing hydrophilic head-group was prepared in a similar way to compound 3. Briefly, TriBoc-Spermine was reacted with excess of 1-azido-3-iodo-propane in the presence of excess TBA. The resulting quaternarized derivative was hydrogenised under (Pd—C) and Boc protecting group were removed using gaseous HCl in dry methanol.

Workup

  1. customwere removed

Sources & evidence

ORD record
ord-7efc57ded6f7404794f1c0a62996d328
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06958325B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes