Acetic Acid → HCID 117761986, compound

HRID 1474649Notes

Reaction equation

HRID 1474649 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]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][O:37][Si](C(C)(C)C)(C)C)=[CH:30][CH:29]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:45][O:46][C:47](=[O:49])[CH3:48])(=[O:3])[CH3:2].C(O)(=O)C.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[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]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][OH:37])=[CH:32][CH:33]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:45][O:46][C:47](=[O:49])[CH3:48])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 89445477HCID 89445477, compound

Product 1

HCID 117761986HCID 117761986, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyl dimethyl silyl)oxy)ethoxy)benzyl)-4-cyanophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (180.0 mg, 0.25 mmol), was added acetic acid (1.5 mL) and water (0.5 mL) and the reaction mixture was stirred overnight at r.t. After the completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethyl acetate (50 mL) followed by neutralization with sodium bicarbonate solution till effervescence ceased. The organic layer was separated, washed with water (2×20 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 3:2 EtOAc:Pet Ether) to afford title compound (140.0 mg, 95%) as a solid.

Workup

  1. customAfter the completion of the reaction
  2. customThe organic layer was separated
  3. washwashed with water (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford crude product which
  7. customwas purified by column chromatography (silica gel, 3:2 EtOAc:Pet Ether)

Sources & evidence

ORD record
ord-94d36e4493ed4020b92d4765b73f3adc
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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