Ethanol → HCID 131732774, compound

HRID 1474632Notes

Reaction equation

HRID 1474632 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]C5C(=O)CCC=5)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:7][O:8]2)(=[O:3])[CH3:2].[N:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[CH2:53]([OH:55])C>C(OC(=O)C)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][C:48]5[C:52](=[N:47][O:55][CH3:53])[CH2:51][CH2:50][CH:49]=5)=[CH:33][CH:34]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:7][O:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 117761396HCID 117761396, compound

Product 1

HCID 131732774HCID 131732774, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-((5-oxocyclopent-1-en-1-yl)oxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (150 mg, 0.22 mmol) in ethanol (1.14 mL), O-methoxylamine.hydrochloride (35 mg, 0.45 mmol) and pyridine (0.91 mL, 1.14 mmol) were added. The reaction mixture was heated to 100° C. for 1 h. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and the mixture was washed with 2% HCl (2×10 mL), water (50 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1.5:8.5 Acetone:hexane) to provide title compound (110 mg, 70.2%) as off-white solid.

Workup

  1. customAfter completion of the reaction
  2. washthe mixture was washed with 2% HCl (2×10 mL), water (50 mL) and brine (20 mL) successively
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 1.5:8.5 Acetone:hexane)

Sources & evidence

ORD record
ord-8cb61b2917ec49adb733eaf2bfc4eaab
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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