Toluene → [1-(dibenzyl)phosphoryloxymethyl-1-hydroxymethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)propyl]carbamic Acid Benzyl Ester

HRID 2406024

Reaction equation

HRID 2406024 reaction equation
[CH2:1]([O:8][C:9](=[O:36])[NH:10][C:11]([CH2:34][OH:35])([CH2:32][OH:33])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:16]([C:28]([F:31])([F:30])[F:29])[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:44][P:45](OP(OCC1C=CC=CC=1)(OCC1C=CC=CC=1)=O)(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.[C:74]1([CH3:80])[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1.F[C:82](F)(F)[C:83](F)(F)[C:84](F)(F)[C:85](F)(F)[C:86](F)(F)[C:87](F)(F)F.Cl[CH2:102]Cl>[I-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.[Ag]=O>[CH2:1]([O:8][C:9](=[O:36])[NH:10][C:11]([CH2:34][O:35][P:45]([CH2:82][C:83]1[CH:102]=[CH:87][CH:86]=[CH:85][CH:84]=1)([CH2:80][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)=[O:44])([CH2:32][OH:33])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:16]([C:28]([F:31])([F:30])[F:29])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 6344DichloromethaneHCID 9639PerfluorohexaneHCID 563183Tetrabenzyl pyrophosphateHCID 57704545[1,1-bis(hydroxymethyl)-3-(4-heptyloxy-3-trifluoromethylphenyl)propyl]carbamic Acid Benzyl Ester

Product 1

HCID 67417982[1-(dibenzyl)phosphoryloxymethyl-1-hydroxymethyl-3-(4-heptyloxy-3-trifluoromethylphenyl)propyl]carbamic Acid Benzyl Ester

Reagents, catalysts & solvents 2

HCID 75056Tetrahexylammonium iodideCatalystHCID 92152Silver(II) oxideCatalyst

Procedure

Compound 2-1 (230 mg), pyrophosphoric acid tetrabenzyl ester (485 mg), silver oxide (208 mg) and tetra-n-hexyl ammonium iodide (433 mg) were added to a mixed solvent of toluene (4 ml), dichloromethane (4 ml) and perfluorohexane (4 ml), and the mixture was stirred at room temperature for 15 hr. Insoluble material was filtered off and the solvent was evaporated under reduced pressure. The residue was purified by preparative HPLC to give the object product (210 mg) as a colorless oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cf6720065eae450ea255bf8545574cdc
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Linked notes

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