Triethylamine → 4-{4-[(Tert-butoxycarbonyl)(methyl)amino]butanoyl}benzyl methanesulfonate

HRID 446572Notes

Reaction equation

HRID 446572 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:22])[CH2:10][CH2:11][CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>ClCCl>[CH3:30][S:31]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:22])[CH2:10][CH2:11][CH2:12][N:13]([C:14]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:20])[CH3:21])=[CH:5][CH:4]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86663464tert-Butyl {4-[4-(hydroxymethyl)phenyl]-4-oxobutyl}methylcarbamate

Product 1

HCID 866634654-{4-[(Tert-butoxycarbonyl)(methyl)amino]butanoyl}benzyl methanesulfonateYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (651 mg, 2.12 mmol) obtained in Example 78a was dissolved in dichloromethane (20 mL), triethylamine (0.590 mL, 4.24 mmol) and methanesulfonyl chloride (0.245 mL, 3.18 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude 4-{4-[(tert-butoxycarbonyl)(methyl)amino]butanoyl}benzyl methanesulfonate (851 mg) as a yellow oily substance.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6f63741b49714124831c69300500b305
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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