Acetic Acid → HCID 117762492, compound

HRID 1474613Notes

Reaction equation

HRID 1474613 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][O:38][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2].C(O)(=O)C>C1COCC1.O>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][OH:38])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 89442788HCID 89442788, compound

Product 1

HCID 117762492HCID 117762492, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution (2S,3S,4R,5S,6S)-2-(3-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)benzyl)-4-chlorophenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (300 mg, 0.452 mmol) in THF:Water (1:1, 3.2 mL) was added acetic acid (4.8 mL) at 0° C. The reaction mixture was stirred at r.t. for 24 h. After completion of reaction, as confirmed by TLC, the reaction mixture was evaporated in vacuo and the residue obtained was purified by column chromatography (silica gel, 1:1 Ethyl acetate:Pet. Ether) to afford title compound (176 mg, 80%).

Workup

  1. customAfter completion of reaction
  2. customthe reaction mixture was evaporated in vacuo
  3. customthe residue obtained
  4. customwas purified by column chromatography (silica gel, 1:1 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-09733432c4bd4bfb8c9f21f38d47eb1e
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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