Benzyl Alcohol → HCID 53760467, compound

HRID 1110271Notes

Reaction equation

HRID 1110271 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]=[C:15](C(O)=O)[CH:14]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:48])C=CC=CC=1.C([N:60]([CH2:63]C)CC)C.[CH2:65]([OH:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>C1(C)C=CC=CC=1>[C:66]1([CH2:65][O:72][C:63](=[O:48])[NH:60][C:15]2[CH:16]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:18]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:5][CH2:6][CH3:7])=[O:8])[CH:14]=2)[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 54209232HCID 54209232, compound

Product 1

HCID 53760467HCID 53760467, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2.55 g (4.36 mmol) of 3-[3-carboxy-5-(octadecyloxy)phenoxy]propylphosphonic acid diethyl ester in 75 ml of toluene stirred and cooled in an ice bath was added 1.12 ml (5.23 mmol) of diphenylphosphoryl azide followed by 0.73 ml (5.23 mmol) of triethylamine added dropwise. After stirring in the ice bath for 2 hours, the reaction mixture was stirred and heated at 90° for 2 hours. Benzyl alcohol (16 ml) was added and heating at 90° was continued for 4 hours. The solvent and the excess benzyl alcohol were removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with NaHCO3 solution, dried and concentrated at reduced pressure to an oil which was purified by HPLC using 50% ethyl acetate-hexane to give 2.47 g (82% yield) of [3-[3-(diethoxyphosphinyl)propoxy]-5-(octadecyloxy)-phenyl]carbamic acid phenylmethyl ester as an oil. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperaturecooled in an ice bath
  2. additionadded dropwise
  3. temperatureheated at 90° for 2 hours
  4. temperatureheating at 90°
  5. customThe solvent and the excess benzyl alcohol were removed at reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe extract was washed with NaHCO3 solution
  8. customdried
  9. concentrationconcentrated at reduced pressure to an oil which
  10. customwas purified by HPLC

Sources & evidence

ORD record
ord-f65eb66d446d42c3a94322442580a42d
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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