Triethylamine → HCID 21019513, compound

HRID 1744786Notes

Reaction equation

HRID 1744786 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.[P:8]([Cl:18])(Cl)(=[O:16])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.C[O:21][C:22](=[O:26])[C@H](C)N>C(Cl)Cl>[P:8]([Cl:18])(=[O:16])([O:26][C:22](=[O:21])[C@H:6]([CH3:7])[NH:3][CH3:4])[O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 21019513HCID 21019513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

A solution of triethylamine (1 ml- 7.17 mmol) in 15 ml of dry CH2Cl2 was added dropwise to a mixture of phenyl phosphorodichloridate (757.4 mg, 3.59 mmol) and L-alanine methyl ester hydrochloride (500 mg, 3.58 mmol) in 50 ml of dry CH2Cl2 at −80° C. in one hour. The mixture was then stirred vigorously at −50° C. during five hours and CH2Cl2 evaporated. 25 ml of dry ether was added and precipitate filtered off under nitrogen. Evaporation of ether gave a colourless oil which was used without further purification for the next step.

Workup

  1. customCH2Cl2 evaporated
  2. addition25 ml of dry ether was added
  3. filtrationprecipitate filtered off under nitrogen
  4. customEvaporation of ether
  5. customgave a colourless oil which
  6. customwas used without further purification for the next step

Sources & evidence

ORD record
ord-39035ac774b44b16a7eab1e618d34c15
Source dataset
uspto-grants-2006_03
Patent number
US07018989B2

Reaction notes

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