Triethylamine → HCID 131720033, compound

HRID 1682778Notes

Reaction equation

HRID 1682778 reaction equation
[C:1]([O:4][C:5](=[O:17])[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[OH:7])(=[O:3])[CH3:2].[C:18]([O:21][CH2:22]Br)(=[O:20])[CH3:19].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:18]([O:21][CH2:22][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])([OH:7])[C:5]([O:4][C:1](=[O:3])[CH3:2])=[O:17])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68536Bromomethyl acetateHCID 88367835HCID 88367835, compound

Product 1

HCID 131720033HCID 131720033, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A pale brown solution of O-Acetyl-2-nitromandelic acid (23) (14 mg, 0.059 mmol), bromomethyl acetate (10 μL, 0.10 mmol), and triethylamine (10 μL, 0.072 mmol) in chloroform (1 mL) is incubated overnight. The volatiles are removed in vacuo, and the residue is purified by flash chromatography (chloroform) to give 16 mg of the title compound (24) as a clear colorless oil, Rf 0.65 (5% MeOH/chloroform.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is purified by flash chromatography (chloroform)

Sources & evidence

ORD record
ord-50cf6b3d18d34b958070cb72acfaa93f
Source dataset
uspto-grants-1997_06
Patent number
US05635608

Reaction notes

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