Triethylamine → tert.-Butyl 3-[(2,3-dichlorobenzenesulphonyl)methylamino]propionate

HRID 1591743Notes

Reaction equation

HRID 1591743 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>O1CCCC1>[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[S:20]([CH2:1][NH:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 14760311Tert-butyl 3-(methylamino)propanoate

Product 1

HCID 69423846tert.-Butyl 3-[(2,3-dichlorobenzenesulphonyl)methylamino]propionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (6.28 mmol) of tert.-butyl N-methyl-β-alaninate, 1.54 g (6.28 mmol) of 2,3-dichlorobenzenesulphonyl chloride and 0.70 g (6.92 mmol) of triethylamine in 30 ml of tetrahydrofuran was stirred at room temperature overnight and then evaporated to dryness. About 50 ml of water were added to the residue, and the mixture was extracted three times with in each case 20 ml of ethyl acetate. The organic extracts were washed with about 20 ml of saturated sodium chloride solution and then evaporated to dryness. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: dichloromethane).

Workup

  1. customevaporated to dryness
  2. additionAbout 50 ml of water were added to the residue
  3. extractionthe mixture was extracted three times with in each case 20 ml of ethyl acetate
  4. washThe organic extracts were washed with about 20 ml of saturated sodium chloride solution
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-83479e9e05ef4a03b00bff159067cec7
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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