Diethyl Ether → HCID 53924627, compound

HRID 1759299Notes

Reaction equation

HRID 1759299 reaction equation
C([N:3]([CH2:8][P:9]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])[CH2:4][C:5]([OH:7])=[O:6])C.[N:25]12[CH2:35]C[CH2:33][CH2:32][CH:31]1C=N[CH2:28][CH2:27][CH2:26]2.O1CC[CH2:38][CH2:37]1.CC[O:43]CC>>[CH2:37]([O:7][C:5](=[O:6])[CH2:4][N:3]([C:35]([N:25]([CH:26]=[CH:27][CH3:28])[CH:31]=[CH:32][CH3:33])=[O:43])[CH2:8][P:9]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([O:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:10])[CH3:38]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20531557HCID 20531557, compound

Product 1

HCID 53924627HCID 53924627, compoundYield 19.3%

Conditions

Temperature
26 °C

Procedure

N',N'-Dipropenylaminocarbonyl chloride (5.6 g; 0.035 mol.) was added to a mixture of ethyl-N-diphenoxyphosphinylmethylglycine (8.4 g; 0.026 mol.) and 1,5-diazabicyclo[5.4.0]undec-5-ene (5.47 g; 0.036 mol.) in 50 ml. of tetrahydrofuran. The reaction mixture was stirred at 26° C. under a nitrogen atmosphere for 64 hours. The reaction mixture was concentrated in vacuo and the resulting residue was diluted with chloroform. The chloroform solution was washed with water, dried over magnesium sulfate and concentrated in vacuo to yield a crude product. The crude product was chromatographically purified employing a silica gel column and a 1:1 mixture (by volume) of cyclohexane:ethylacetate as the eluent to yield an impure product which was then dissolved in ether. The ether solution was washed with a 2% sodium hydroxide solution, water, dried over magnesium sulfate and concentrated in vacuo to yield ethyl-N-[N',N'-dipropenylaminocarbonyl]-N-diphenoxyphosphinylmethylglycinate (2.2 g; 19.3%) represented by the formula ##STR14## as an oil having the following analysis:

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resulting residue was diluted with chloroform
  3. washThe chloroform solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield a crude product
  7. customThe crude product was chromatographically purified
  8. customa 1:1 mixture (by volume) of cyclohexane:ethylacetate as the eluent to yield an impure product which
  9. washThe ether solution was washed with a 2% sodium hydroxide solution, water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50546403c4aa407c9d9cab7ea12c4e56
Source dataset
uspto-grants-1982_07
Patent number
US04340416

Reaction notes

Loading…