Triethylamine → HCID 57847161, compound

HRID 1009944Notes

Reaction equation

HRID 1009944 reaction equation
[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[NH:28][C:29]([NH:31][CH2:32][CH2:33][C:34](O)=[O:35])=[O:30])=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].C([N:41](CC)CC)C.C(OP(C#N)(=O)OCC)C.C(=O)([O-])O.[Na+]>CN(C=O)C.O>[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[NH:28][C:29]([NH:31][CH2:32][CH2:33][C:34]([NH2:41])=[O:35])=[O:30])=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 57847082HCID 57847082, compound

Product 1

HCID 57847161HCID 57847161, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (0.171 g, 0.348 mmol) synthesized in Example 157, ammonium chloride (0.0261 g, 0.488 mmol), triethylamine (0.0685 ml, 0.488 mmol) and diethylcyanophosphonate (0.07 ml, 0.418 mmol) were stirred in DMF (5 ml) under ice-cooling for 1 hr and at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution and water were added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using basic silica gel (30 g) and eluted with ethyl acetate-methanol (1:0-4:1, v/v) to give the title compound (0.117 g, 69%) as an amorphous form from the object fraction.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (over anhydrous MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. washeluted with ethyl acetate-methanol (1:0-4:1

Sources & evidence

ORD record
ord-818960d171df4321becae07bfc595e9c
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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