Triethylamine → HCID 68461169, compound

HRID 2357951Notes

Reaction equation

HRID 2357951 reaction equation
[CH2:1]([C:3]1[CH:16]=[C:6]2[C:7]([C:13]([OH:15])=O)=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[N:5]2[N:4]=1)[CH3:2].Cl.CN[O:20][CH3:21].C(P(=O)(OCC)OCC)#N.C([N:34]([CH2:37]C)CC)C>CN(C)C=O.O>[CH3:21][O:20][CH2:37][NH:34][C:13]([C:7]1[C:6]2[N:5]([N:4]=[C:3]([CH2:1][CH3:2])[CH:16]=2)[C:10]([O:11][CH3:12])=[CH:9][CH:8]=1)=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 59389311HCID 59389311, compound

Product 1

HCID 68461169HCID 68461169, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound of Example 348 (11.13 g) was dissolved in N,N-dimethylformamide (505 mL) in an argon atmosphere. While this solution was chilled in an ice bath, N,O-dimethylhydroxyamine hydrochloride (6.15 g) and diethyl cyanophosphonate were added, followed by dropwise addition of triethylamine (17.5 mL). The mixture was stirred first in an ice bath for 30 min and then at room temperature for 5 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel chromatography (ethyl acetate) afforded the title compound as a brown oil (12.12 g).

Workup

  1. temperatureWhile this solution was chilled in an ice bath
  2. waitat room temperature for 5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customEvaporation of the solvent and subsequent purification of the residue by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e2d82a5667b74a54b06a5155fcec61e7
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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