Trityl chloride → HCID 70872926, compound

HRID 1914501Notes

Reaction equation

HRID 1914501 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]3[CH:13]=[C:14]([C@H:20]4[C@H:25]([OH:26])[C@@H:24]([OH:27])[C@H:23]([OH:28])[C@@H:22]([CH2:29][OH:30])[O:21]4)[CH:15]=[CH:16][C:17]=3[CH2:18][CH3:19])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]3[CH:13]=[C:14]([C@H:20]4[C@H:25]([OH:26])[C@@H:24]([OH:27])[C@H:23]([OH:28])[C@@H:22]([CH2:29][O:30][C:31]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)[C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)[O:21]4)[CH:15]=[CH:16][C:17]=3[CH2:18][CH3:19])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 52913524Licogliflozin2×

Product 1

HCID 70872926HCID 70872926, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (2S,3R,4R,5S,6R)-2-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (Intermediate 2, 6.0 g, 14.40 mmol) in pyridine (60 ml) was added trityl chloride (4.8 g, 17.28 mmol) followed by DMAP (0.18 g, 1.44 mmol) at room temperature. Then the reaction mixture was heated at 80° C. After stirring for 16 h, pyridine was evaporated under reduced pressure. Resulting residue was taken in ethyl acetate (100 ml), washed with aq. copper sulfate solution (50 ml), brine (100 ml), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to give 8.10 g of (2S,3R,4R,5S,6R)-2-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol as white solid.

Workup

  1. custompyridine was evaporated under reduced pressure
  2. washwashed with aq. copper sulfate solution (50 ml), brine (100 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a788e26ad38414fa646e1222b6eed1c
Source dataset
uspto-grants-2013_12
Patent number
US08614195B2

Reaction notes

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