Triethylamine → tert-butyl N-(12-mesyloxydodecyl)carbamate

HRID 1003313Notes

Reaction equation

HRID 1003313 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[S:22](Cl)([CH3:25])(=[O:24])=[O:23].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1>[C:15]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:22]([CH3:25])(=[O:24])=[O:23])([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 3613308Tert-butyl N-(12-hydroxydodecyl)carbamate

Product 1

HCID 18796422tert-butyl N-(12-mesyloxydodecyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.96 g of tert-butyl N-(12-hydroxydodecyl)carbamate in 60 ml of tetrahydrofuran were successively added dropwise under ice-cooling 2.1 ml of mesyl chloride and 3.8 ml of triethylamine and the mixture was stirred for one hour. To the reaction solution was added ethyl acetate and the mixture was washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate, water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to afford 8.06 g of the title compound.

Workup

  1. washthe mixture was washed successively with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-35815c04597541bbb67a2f364b5cabef
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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