Water → HCID 71655302, compound

HRID 270127Notes

Reaction equation

HRID 270127 reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[N+](C1C=C(S(O[CH2:36][C@@H:37]2[CH2:39][O:38]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1C(=O)CCC1>[Cl:1][C:2]1[C:3]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:4][C:5]([O:12][CH2:36][C@@H:37]2[CH2:39][O:38]2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 57428728HCID 57428728, compound

Product 1

HCID 71655302HCID 71655302, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of methyl 5-chloro-2-hydroxy-4-[(4-methoxybenzyl)oxy]benzoate (1.78 g, 5.5 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.43 g, 5.5 mmol) and cesiumcarbonate (2.15 g, 6.6 mmol) in NMP (15 mL) was stirred at room temperture overnight. Water was added to the mixture and it was then extracted with with ethyl acetate three times. The combined organinc layers was washed with water, dried over sodium sulphate and solvent was removed in vacuo. The residue was purified by silica gel flash chromatography (ethyl acetate/heptane 10-30%), (1.66 g, 79%) of the title compound was obtained.

Workup

  1. extractionwas then extracted with with ethyl acetate three times
  2. washThe combined organinc layers was washed with water
  3. dry with materialdried over sodium sulphate and solvent
  4. customwas removed in vacuo
  5. customThe residue was purified by silica gel flash chromatography (ethyl acetate/heptane 10-30%)

Sources & evidence

ORD record
ord-83122fd706f64cfbbd023305de101963
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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