Benzyl Alcohol → HCID 54488810, compound

HRID 1757785Notes

Reaction equation

HRID 1757785 reaction equation
[O:1]=[C:2]([NH:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([NH:22][C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:21]=1)C(O)=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])C=CC=CC=1.C([N:53]([CH2:56]C)CC)C.[CH2:58]([OH:65])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>C1(C)C=CC=CC=1>[C:59]1([CH2:58][O:65][C:56](=[O:41])[NH:53][C:15]2[CH:19]=[C:20]([NH:22][C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:21]=[C:13]([NH:12][C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:14]=2)[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 152328323,5-Bis[(1-oxodecyl)amino]benzoic acid

Product 1

HCID 54488810HCID 54488810, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 5.0 g (10.85 mmol) of 3,5-bis[(1-oxodecyl)amino]benzoic acid in 150 ml of anhydrous toluene cooled in an ice bath and stirred under an argon atmosphere was added 2.8 ml (13.0 mmol) of diphenylphosphoryl azide followed by 1.8 ml (13.0 mmol) of triethylamine. The reaction mixture was stirred in the ice bath for 1.5 hours, at room temperature for 1 hour and then at 90° for 2 hours. Benzyl alcohol (39 ml, 0.38 mol) was added and heating at 90° was continued for 4 hours. The solvent was removed at reduced pressure and most of the excess benzyl alcohol was removed at 80°/1 mm. NaHCO3 solution was added and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure and the residue was purified by HPLC using 25% ethyl acetate-hexane to give 2.78 g (45% yield) of [3,5-bis[(1 -oxodecyl)amino]phenyl]carbamic acid phenylmethyl ester as a yellow foam. The nmr and mass spectra were compatible with the structure.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureheating at 90°
  3. waitwas continued for 4 hours
  4. customThe solvent was removed at reduced pressure and most of the excess benzyl alcohol
  5. customwas removed at 80°/1 mm
  6. additionNaHCO3 solution was added
  7. extractionthe product was extracted with ethyl acetate
  8. extractionThe dried extract
  9. concentrationwas concentrated at reduced pressure
  10. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-ca0625e1b6464aafa00f19c2be6f34a4
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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