Hydrochloric Acid → Cholesterol TREN bis-guanidinium methylphosponamidate

HRID 1987787Notes

Reaction equation

HRID 1987787 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[CH2:29]([NH2:38])[CH2:30][N:31]([CH2:35][CH2:36][NH2:37])[CH2:32][CH2:33][NH2:34].[CH3:39][P:40]([NH2:43])(=[O:42])[O-:41].[N:44]1([C:49]([NH2:51])=[NH:50])C=CC=N1.Cl.C(N(C(C)C)CC)(C)C>CN(C=O)C.ClCCl>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[CH2:29]([NH2:38])[CH2:30][N:31]([CH2:35][CH2:36][NH2:37])[CH2:32][CH2:33][NH2:34].[CH3:39][P:40]([NH2:43])(=[O:41])[O-:42].[NH2:50][C:49]([NH2:51])=[NH2+:44].[NH2:50][C:49]([NH2:51])=[NH2+:44]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2734673PraxadineHCID 131723226Cholesterol TREN methylphosphonamidate

Product 1

HCID 131727501Cholesterol TREN bis-guanidinium methylphosponamidate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Compound (18) (0.148 g, 0.25 mmol) was dissolved in anhydrous DMF (1.0 ml) and anhydrous dichoromethane (5.0 ml). 1-H-pyrazole-1carboxarnidine.HCl (73 mg, 0.50 mmol) was added to the reaction mixture followed by diisopropylethylamine (87 ml, 0.50 mmol). Dichloromethane was stripped off of the reaction mixture on a rotovap then rotation continued overnight without vacuum at room temperature. After removing DMF in vacuo the reaction residue was dissolved in dichloromethane and applied to a flash silica gel column. A gradient of 5 to 20% MeOH/dichloromethane with 0.5 to 2% NH4OH followed by treatment with Dowex OH− (300 mg) in MeOH gave pure (19): 0.11 g, 65%, 31P NMR (d, 33.83 ppm), mass spec. calcd=676.97. Found=677.54.

Workup

  1. customAfter removing DMF in vacuo the reaction residue
  2. dissolutionwas dissolved in dichloromethane

Sources & evidence

ORD record
ord-5097da5523324caa8be8e9d1a5dbe8cd
Source dataset
uspto-grants-2009_06
Patent number
US07553830B2

Reaction notes

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