Pyridine → HCID 117761600, compound

HRID 1474642Notes

Reaction equation

HRID 1474642 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][C:36]5[CH:41]=[CH:40][C:39]([C:42](=O)[CH3:43])=[CH:38][CH:37]=5)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:45][O:46][C:47](=[O:49])[CH3:48])[CH2:7][O:8]2)(=[O:3])[CH3:2].N1C=CC=CC=1.Cl.[CH2:57]([O:59][NH2:60])[CH3:58]>C(O)C.C(OCC)(=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:34]=[CH:33][C:32]([O:35][C:36]5[CH:41]=[CH:40][C:39]([C:42](=[N:60][O:59][CH2:57][CH3:58])[CH3:43])=[CH:38][CH:37]=5)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:45][O:46][C:47](=[O:49])[CH3:48])[CH2:7][O:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 117762538HCID 117762538, compound

Product 1

HCID 117761600HCID 117761600, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(4-acetylphenoxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (300.0 mg, 0.43 mmol) in ethanol (5 mL) under nitrogen atmosphere, was added pyridine (0.17 mL, 2.15 mmol) and O-ethylhydroxylamine hydrochloride (84.0 mg, 0.86 mmol). The reaction mixture was heated at 80° C. for 4 h. After completion of the reaction as confirmed by TLC, the crude compound was diluted with ethyl acetate (2×20 mL). The organic layer was separated, washed with 5% HCl (10 mL), water (10 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1:4 EtOAc:Pet Ether) to afford the title compound (230.0 mg, 72%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. customThe organic layer was separated
  3. washwashed with 5% HCl (10 mL), water (10 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, 1:4 EtOAc:Pet Ether)

Sources & evidence

ORD record
ord-e7c176ba3a6e46f7b5004df7a48c2008
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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