Dichloromethane → HCID 86759495, compound

HRID 1884328Notes

Reaction equation

HRID 1884328 reaction equation
C(O[C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[F:38][C:39]([F:51])([F:50])[C:40]([NH:42][C:43]1[CH:44]=[C:45]([OH:49])[CH:46]=[CH:47][CH:48]=1)=[O:41].B(F)(F)F.ClCCl>O1CCCC1>[C:8]([O:7][C@@H:6]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C@H:5]1[O:49][C:45]1[CH:46]=[CH:47][CH:48]=[C:43]([NH:42][C:40](=[O:41])[C:39]([F:50])([F:51])[F:38])[CH:44]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6356Boron trifluorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 23505419Acetamide, 2,2,2-trifluoro-N-(3-hydroxyphenyl)-

Product 1

HCID 86759495HCID 86759495, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (500 mg, 0.99 mmol), 3-trifluoroacetamidophenol (407 mg, 1.98 mmol) from Stage 1 and boron trifluoride diethyletherate (1.41 g, 9.93 mmol, 1.25 ml) in a mixture of dry dichloromethane (10 ml) and dry tetrahydrofuran (30 ml) was stirred at room temperature under argon for 7 days. Work-up as in Stage 1 of Example 1 and purification by flash chromatography on silica gel (2% acetone in toluene as eluant) gave the title compound as a colourless solid (166 mg. 21%).

Workup

  1. customWork-up as in Stage 1 of Example 1 and purification by flash chromatography on silica gel (2% acetone in toluene as eluant)

Sources & evidence

ORD record
ord-e2e2cd5d6fa241ffb2663bd4c262962f
Source dataset
uspto-grants-2004_07
Patent number
US06764829B2

Reaction notes

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