Dichloromethane → 156591-79-6

HRID 1756021Notes

Reaction equation

HRID 1756021 reaction equation
[C:1]([O:5][C:6]([N:8]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:9][CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)Cl>CS(C)=O>[C:1]([O:5][C:6]([N:8]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:9][CH:10]=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 19916832HCID 19916832, compound

Product 1

HCID 21955213156591-79-6Yield 94.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To N-tert-butoxycarbonyl-N-tert-butylethanolamine (7.24 g), triethylamine (13.5 g) and methylene chloride (150 ml) in 500 ml round bottom flask, a solution dissolved sulfur trioxide-pyridine complex (15.9 g) into 150 ml of DMSO was added at a time under cooling with ice and stirring. After stirring for 10 minutes at room temperature, the reaction mixture was poured into 1 liter of saturated saline solution. After the methylene chloride layer was separated, the aqueous layer was extracted with ether and all of the organic layers were combined, which was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by means of silica gel chromatography (chloroform: ethanol=20:1) to obtain 6.80 g of aimed product as a faintly yellow oily product. Yield: 94.8%

Workup

  1. additionwas added at a time
  2. temperatureunder cooling with ice
  3. stirringAfter stirring for 10 minutes at room temperature
  4. customAfter the methylene chloride layer was separated
  5. extractionthe aqueous layer was extracted with ether
  6. dry with materialwhich was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by means of silica gel chromatography (chloroform: ethanol=20:1)

Sources & evidence

ORD record
ord-630c17170e644ee98754b308c509acf1
Source dataset
uspto-grants-1995_08
Patent number
US05439919

Reaction notes

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