Diisopropylethylamine → HCID 178443925, compound

HRID 1987785Notes

Reaction equation

HRID 1987785 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].[NH2:29][C@H:30]([C:36]([OH:38])=[O:37])[CH2:31][CH2:32][CH2:33][CH2:34][NH2:35].[CH3:39][P:40]([NH2:43])(=[O:42])[O-:41].C([N:47]([CH:50](C)C)CC)(C)C>CN(C=O)C>[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].[NH2:29][C@H:30]([C:36]([OH:38])=[O:37])[CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:50]([NH2:47])=[NH:43].[CH3:39][P:40]([NH2:43])(=[O:41])[O-:42]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 86587670HCID 86587670, compound

Product 1

HCID 178443925HCID 178443925, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (15) (0.131 g, 0.216 mmol) stirring at room temperature under argon in anhydrous DMF (2.0 ml), 1-H-pyrazole-1-carboxamidine•HCl (32 mg, 0.216 mmol) was added followed by diisopropylethylamine (28 ml, 0.216 mmol). The reaction mixture was stripped slightly on a rotovap then rotated 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. An isocratic system of 20% MeOH/dichloromethane, 2% NH4OH followed by treatment with Dowex OH− (300 mg) in MeOH gave 80 mg of desired product (yield, 57%). 31P NMR (s, 31.99 ppm), mass spec. calcd=648.91, Found=649.48.

Workup

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

Sources & evidence

ORD record
ord-2715ac417aa24628a429926983a95556
Source dataset
uspto-grants-2009_06
Patent number
US07553830B2

Reaction notes

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