Water → HCID 86612856, compound

HRID 1782036Notes

Reaction equation

HRID 1782036 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[N+](C1C=C(S(O[CH2:23][C@@H:24]2[CH2:26][O:25]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[O:25]1[CH2:26][C@H:24]1[CH2:23][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 86612856HCID 86612856, compoundYield 114.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Salicylaldehyde (486 mg, 3.99 mmol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (900 mg, 3.47 mmol) was dissolved in DMF (5 ml) and Cs2CO3 (1.28 g, 3.94 mmol) was added. The reaction mixture stirred for 12 at room temperature. Water (100 ml) was added, and the mixture was extracted with DCM (2×50 ml). The combined organic extracts were washed with water (2×50 ml). The volatiles were removed in vacuo to give the subtitle compound (76%, 710 mg), which was used directly in the next step.

Workup

  1. extractionthe mixture was extracted with DCM (2×50 ml)
  2. washThe combined organic extracts were washed with water (2×50 ml)
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-bfba348b0a4443798a1486787f9034d3
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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