Triethylamine → N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine

HRID 1506750Notes

Reaction equation

HRID 1506750 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:16])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3366758Benzyl N-(4-hydroxybutyl)carbamate

Product 1

HCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamineYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of benzyl 4-hydroxybutylcarbamate (1.1 g, 4.9 mmol) and triethylamine (1.7 mL, 9.8 mmol) in THF was added methanesulfonyl chloride (0.67 g, 5.9 mmol) at 0° C. The reaction was stirred at 20-25° C. for 6 hours and concentrated. The residue was partitioned between ethyl acetate and water. The phases were separated, and the organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline. The separated organic layer was dried and concentrated to give 4-(benzyloxycarbonylamino)butyl methanesulfonate (1.2 g).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. washthe organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline
  5. customThe separated organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b20122d48fe34482a3c16ad8d8803456
Source dataset
uspto-grants-2015_12
Patent number
US09221760B2

Reaction notes

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