Triethylamine → HCID 20791939, compound

HRID 2243109Notes

Reaction equation

HRID 2243109 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[CH:5]([CH3:7])[NH2:6].C(N(CC)CC)C.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17]>ClCCl>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([NH:6][CH:5]([CH3:7])[C:4]([O:3][CH3:2])=[O:8])(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 2756298Alanine, methyl ester, hydrochloride (1:1)

Product 1

HCID 20791939HCID 20791939, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DL-Alanine methyl ester hydrochloride (13.96 g; 0.1 mol) is dissolved in 800 ml of dichloromethane and placed at 0° C. Triethylamine (2.3 eq.; 230 mmol; 32 ml) is added dropwise, along with portionwise addition of 2-nitrobenzenesulfonyl chloride (1 eq.; 100 mmol; 22.16 g), and the reaction medium is allowed to return to room temperature overnight. The reaction medium is washed with water and then dried over sodium sulfate, filtered through silica and evaporated to dryness to give 25.3 g of solid corresponding to the title compound.

Workup

  1. customplaced at 0° C
  2. washThe reaction medium is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through silica
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b862b8a51e874d1e956c634a49e0c6ae
Source dataset
uspto-grants-2010_03
Patent number
US07674803B2

Reaction notes

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