Triethylamine → 3-((Tert-butoxycarbonyl)(methyl)amino)propyl methanesulfonate

HRID 446580Notes

Reaction equation

HRID 446580 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:13])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)([O-])O.[Na+]>ClCCl>[CH3:21][S:22]([O:1][CH2:2][CH2:3][CH2:4][N:5]([C:6]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:12])[CH3:13])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 10375241tert-Butyl (3-hydroxypropyl)methylcarbamate

Product 1

HCID 197540213-((Tert-butoxycarbonyl)(methyl)amino)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (3-hydroxypropyl)methylcarbamate (551 mg, 2.92 mmol) was dissolved in dichloromethane (15 mL), triethylamine (0.811 mL, 5.83 mmol) and methanesulfonyl chloride (0.337 mL, 4.38 mmol) were added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, the mixture was extracted with methylene chloride, and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was purified by short-path silica gel column chromatography (elution solvents, n-hexane:ethyl acetate=1:1→0:1, v/v) to give crude 3-([tert-butoxycarbonyl)(methyl)amino]propyl methanesulfonate as a colorless oily substance. The resulting crude product was dissolved in ethanol (15 mL), N,N-diisopropylethylamine (5.07 mL, 29.2 mmol) and methoxyamine hydrochloride (2.43 g, 29.2 mmol) were added, and the mixture was stirred at 50° C. for 14 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, the mixture was extracted with methylene chloride, and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (elution solvents, n-hexane:ethyl acetate:methanol=9:1:0→0:1:0→0:9:1, v/v/v) to give the title compound (362 mg; yield, 19%).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialthe resulting organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by short-path silica gel column chromatography (
  5. washelution solvents, n-hexane

Sources & evidence

ORD record
ord-30bc0cdb75a2401eb9234610f6624ca5
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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