Benzyl Alcohol → HCID 19969644, compound

HRID 974822Notes

Reaction equation

HRID 974822 reaction equation
[C:1]1([C:7]([CH2:18][CH2:19][CH2:20][CH:21]2[O:25][CH2:24][CH2:23][O:22]2)([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:28]([CH2:31]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.[CH2:50]([OH:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1(C)C=CC=CC=1>[C:31]([NH:28][C:7]([CH2:18][CH2:19][CH2:20][CH:21]1[O:22][CH2:23][CH2:24][O:25]1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([O:57][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:40]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19969600HCID 19969600, compound

Product 1

HCID 19969644HCID 19969644, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The acid of step (a) (25 g), triethylamine (11.2 ml) and diphenylphosphoryl azide were dissolved in dry toluene (400 ml) and heated at reflux for 3 hours. Benzyl alcohol (30.4 ml) was added dropwise and the resulting mixture was refluxed overnight. Concentration of the reaction mixture afforded a dark oil which was purified by chromatography on silica gel and elution with ethyl acetate/hexanes [1:9-1:1]to give the subtitle compound (25 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperaturethe resulting mixture was refluxed overnight
  4. customConcentration of the reaction mixture afforded a dark oil which
  5. customwas purified by chromatography on silica gel and elution with ethyl acetate/hexanes [1:9-1:1]to

Sources & evidence

ORD record
ord-38e3f3b295f94630a70a0244ad551955
Source dataset
uspto-grants-1997_03
Patent number
US05607935

Reaction notes

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