Trifluoromethanesulfonic acid → HCID 86595232, compound

HRID 350760Notes

Reaction equation

HRID 350760 reaction equation
[C:1]([O:9][C@@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:13]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:12][C@H:11]1SCCNC(=O)OCC1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:58][CH2:59][CH:60]([NH:65][C:66](=[O:84])[CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[C:61]([O:63][CH3:64])=[O:62].IN1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>C(Cl)(Cl)Cl>[C:66]([NH:65][CH:60]([CH2:59][O:58][C@@H:11]1[O:12][C@H:13]([CH2:34][O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:14]([O:25][C:26](=[O:33])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:10]1[O:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:61]([O:63][CH3:64])=[O:62])(=[O:84])[CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83]

Participants

6

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 22935277HCID 22935277, compoundHCID 68866814HCID 68866814, compound

Product 1

HCID 86595232HCID 86595232, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

In 35 mL of chloroform were dissolved 2.4 g of benzyl 2-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosylthio)ethylcarbamate and 1 g of methyl 3-hydroxy-2-(octadecanoylamino)propionate, and after cooling the solution to 0° C., 1.4 g of N-iodosuccinimide and 0.13 mL of trifluoromethanesulfonic acid were added to the solution and the resulting mixture was stirred at room temperature for 3 hours. Then, chloroform was added to the reaction mixture, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and 10% aqueous sodium thiosulfate solution. The chloroform layer was dried over anhydrous magnesium sulfate, magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (Eluent; n-hexane:ethyl acetate=3:1) to obtain 1.4 g of methyl 2-(octadecanoylamino)-3-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy)propionate.

Workup

  1. washthe resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and 10% aqueous sodium thiosulfate solution
  2. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Eluent; n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-1dec323b7d92461dab38194f4440afad
Source dataset
uspto-grants-2007_02
Patent number
US07183261B2

Reaction notes

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