Water → HCID 117762239, compound

HRID 1474625Notes

Reaction equation

HRID 1474625 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][C:37](=O)[CH3:38])=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:40][O:41][C:42](=[O:44])[CH3:43])[CH2:7][O:8]2)(=[O:3])[CH3:2].N1C=CC=CC=1.Cl.[CH3:52][O:53][NH2:54].O>C(O)C>[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][C:37](=[N:54][O:53][CH3:52])[CH3:38])=[CH:33][CH:34]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:40][O:41][C:42](=[O:44])[CH3:43])[CH2:7][O:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 117761718HCID 117761718, compound

Product 1

HCID 117762239HCID 117762239, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-oxopropoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (180 mg, 0.28 mmol), in ethanol (8 mL) under nitrogen atmosphere, were added pyridine (0.114 mL, 1.42 mmol) and O-methylhydroxylamine hydrochloride (72 mg, 0.85 mmol). The reaction mixture was refluxed for 2 h. After completion of the reaction as confirmed by TLC, water (10 mL) was added to the reaction mixture and the crude compound was extracted with ethyl acetate (3×25 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1.5:8.5 Acetone:Pet. Ether) to afford the title compound (120 mg, 63.8%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customAfter completion of the reaction
  3. additionwas added to the reaction mixture
  4. extractionthe crude compound was extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford crude product which
  8. customwas purified by column chromatography (silica gel, 1.5:8.5 Acetone:Pet. Ether)

Sources & evidence

ORD record
ord-1e264d5d5db148c4955434fd5e866a8e
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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