Ethanethiol → HCID 18387080, compound

HRID 2296585Notes

Reaction equation

HRID 2296585 reaction equation
[C:1]([O:5][CH:6]([C:20]([OH:22])=[O:21])[N:7]([CH2:17][CH2:18]Br)[CH:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:32]([SH:34])[CH3:33]>ClCCl>[C:1]([O:5][CH:6]([C:20]([OH:22])=[O:21])[N:7]([CH2:17][CH2:18][S:34][CH2:32][CH3:33])[CH:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 81531DiisopropylethylamineHCID 18387081HCID 18387081, compound

Product 1

HCID 18387080HCID 18387080, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.52 g (10 mmol) of N,N-bis-(tert-butoxycarboxy-methyl)-2-bromoethylamine is dissolved in 50 ml of absolute dichloromethane and mixed with 1.29 g (10 mmol) of diisopropylethylamine and 0.621 g (10 mmol) of ethylmercaptan. The reaction mixture is refluxed overnight. Then, the solution is extracted twice with semi-saturated, aqueous sodium bicarbonate solution. The organic phase is dried on sodium sulfate, and the solvent is evaporated in a vacuum. The residue is chromatographed on silica gel (eluant: dichloromethane/methanol 99:1).

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. extractionThen, the solution is extracted twice with semi-saturated, aqueous sodium bicarbonate solution
  3. customThe organic phase is dried on sodium sulfate
  4. customthe solvent is evaporated in a vacuum
  5. customThe residue is chromatographed on silica gel (eluant: dichloromethane/methanol 99:1)

Sources & evidence

ORD record
ord-dc9f023c1cbc4c21938bae2fa82d8c02
Source dataset
uspto-grants-2002_12
Patent number
US06488909B1

Reaction notes

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