HCID 70907159, compound → HCID 70872921, compound

HRID 1914509Notes

Reaction equation

HRID 1914509 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[O:25][C@H:24]([CH2:26][O:27][P:28](=[O:39])([O:34]C(C)(C)C)[O:29]C(C)(C)C)[C@@H:23]([OH:40])[C@H:22]([OH:41])[C@H:21]4[OH:42])[CH:15]=[CH:16][C:17]=3[CH2:18][CH3:19])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>CO>[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[O:25][C@H:24]([CH2:26][O:27][P:28](=[O:29])([OH:34])[OH:39])[C@@H:23]([OH:40])[C@H:22]([OH:41])[C@H:21]4[OH:42])[CH:15]=[CH:16][C:17]=3[CH2:18][CH3:19])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 70907159HCID 70907159, compound

Product 1

HCID 70872921HCID 70872921, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the stirred solution of phosphoric acid di-tert-butyl ester (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (500 mg) in methanol (20 ml) was added amberlyst 15 ion exchange resin (250 mg) and refluxed for overnight. Reaction mixture was cooled to room temperature, filtered through celite bed and filtrate was concentrated to give 300 mg of phosphoric acid mono-{(2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl}ester. The crude material was taken up for next reaction.

Workup

  1. temperaturerefluxed for overnight
  2. customReaction mixture
  3. filtrationfiltered through celite bed and filtrate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-7681d42a801b47658dee11be5806bf69
Source dataset
uspto-grants-2013_12
Patent number
US08614195B2

Reaction notes

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