Acetic Acid → HCID 89442952, compound

HRID 1474605Notes

Reaction equation

HRID 1474605 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[C@H:11](CC([O-])=O)[C@H:10](CC([O-])=O)[C@H:9](CC([O-])=O)[C@@H:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][O:41][Si](C(C)(C)C)(C)C)=[CH:34][CH:33]=3)[CH:25]=2)[O:7]1)(=[O:3])[CH3:2].[C:49]([OH:52])(=[O:51])[CH3:50]>C1COCC1.O>[C:49]([O:52][C@H:11]1[C@H:10]([O:51][C:49](=[O:52])[CH3:50])[C@@H:9]([O:4][C:1](=[O:3])[CH3:2])[C@H:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][OH:41])=[CH:34][CH:33]=3)[CH:25]=2)[O:7][C@@H:6]1[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:51])[CH3:50]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 131732769HCID 131732769, compound

Product 1

HCID 89442952HCID 89442952, compoundYield 82%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate (2.59 g, 3.66 mmol) in THF:Water (1:1, 36 mL) was added acetic acid (54 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, 4:6 Ethyl acetate:Pet. Ether) to afford title compound (1.8 g, 82%).

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, 4:6 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-f7a7612b3c2c421fbc7ceeeab97dcd0c
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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