Sodium Bicarbonate → (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-hydroxypropoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

HRID 1474624Notes

Reaction equation

HRID 1474624 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]([O:39][Si](C(C)(C)C)(C)C)[CH3:38])=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:47][O:48][C:49](=[O:51])[CH3:50])[CH2:7][O:8]2)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>C(O)(=O)C.C1COCC1.O>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([O:35][CH2:36][CH:37]([OH:39])[CH3:38])=[CH:33][CH:34]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:47][O:48][C:49](=[O:51])[CH3:50])[CH2:7][O:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 131732773HCID 131732773, compound

Product 1

HCID 89442872(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-hydroxypropoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetateYield 65.7%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution (1R,2S,3S,4R,55)-1-(acetoxymethyl)-5-(3-(4-(2-(tert-butyldimethylsilyloxy)propoxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (350 mg, 0.46 mmol) in Acetic acid:THF:Water (3:1:1, 5.0 mL) was stirred at r.t. for 48 h. After completion of the reaction, as confirmed by TLC, sat. solution of NaHCO3 (10 mL) was added dropwise to the reaction mixture and organic layer was extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4 and evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1:1 Ethyl acetate:Pet. Ether) to afford title compound (190 mg, 65.7%).

Workup

  1. customAfter completion of the reaction
  2. additionwas added dropwise to the reaction mixture and organic layer
  3. extractionwas extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (silica gel, 1:1 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-acd9146ecbf64048b5c3f5e961afcac7
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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