Potassium Carbonate → (2S,3R,4S,5S,6S)-2-((S)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoyloxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1513210Notes

Reaction equation

HRID 1513210 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([O:17][C@@H:18]([C:22]([O:35][CH3:36])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([OH:21])=[O:20])[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:43]([O:46][C@@H:47]1[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:51]([O:57][C:58](=[O:60])[CH3:59])[C@@H:50]([C:61]([O:63][CH3:64])=[O:62])[O:49][C@@H:48]1Br)(=[O:45])[CH3:44]>C(#N)C>[C:43]([O:46][C@@H:47]1[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:51]([O:57][C:58](=[O:60])[CH3:59])[C@@H:50]([C:61]([O:63][CH3:64])=[O:62])[O:49][C@H:48]1[O:20][C:19](=[O:21])[C@@H:18]([O:17][C:12]1[N:11]=[C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[C:14]([CH3:16])[N:13]=1)[C:22]([O:35][CH3:36])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 88785Acetobromo-alpha-D-glucuronic acid methyl esterHCID 59441453(s)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoic acid

Product 1

HCID 59441455(2S,3R,4S,5S,6S)-2-((S)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoyloxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetateYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound of Example 14 (0.997 g, 2.05 mmol) in acetonitrile (20 mL) is added potassium carbonate (0.284 g, 2.05 mmol) and the reaction mixture stirred for 0.5 hr. (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.817 g, 2.05 mmol) is added to the reaction mixture and the reaction stirred for 12 hr. The reaction mixture is filtered and the filtrate concentrated under reduced pressure on a rotary evaporator to give a crude product. The crude product is purified by column chromatography on silica gel eluted with ethyl acetate-hexane (2:8) to yield the title compound (1.0 g, 60%). MS m/z 801.1 (M+.+1); 1H NMR (CDCl3, 200 MHz) δ 5.65 (C-6 pyran H, d, J5,6=8 Hz).

Workup

  1. stirringthe reaction stirred for 12 hr
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated under reduced pressure on a rotary evaporator
  4. customto give a crude product
  5. customThe crude product is purified by column chromatography on silica gel
  6. washeluted with ethyl acetate-hexane (2:8)

Sources & evidence

ORD record
ord-21fa2aab2d154a638430c3dca6ee25c8
Source dataset
uspto-grants-2012_07
Patent number
US08217155B2

Reaction notes

Loading…