Triethylamine → (R)-2-t-butoxycarbonylamino-1-hexyl methanesulfonate

HRID 977529Notes

Reaction equation

HRID 977529 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:12][CH2:13][CH2:14][CH3:15])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53987300HCID 53987300, compound

Product 1

HCID 54485960(R)-2-t-butoxycarbonylamino-1-hexyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-t-butoxycarbonylamino-1-hexanol (2.17 g, prepared in (1)) in dichloromethane (20 ml) were added triethylamine (1.67 ml) and methanesulfonyl chloride (0.93 ml) under ice cooling. After being stirred at the same temperature for 1 h, the mixture was washed with water, 10% aq. citric acid, sat. aq NaHCO3 and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=2/1 for elution to give the product (1.32 g).

Workup

  1. washthe mixture was washed with water, 10% aq. citric acid, sat. aq NaHCO3 and brine successively
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=2/1 for elution

Sources & evidence

ORD record
ord-a9432794bab949dc8de1e5f4986cb7f5
Source dataset
uspto-grants-1997_03
Patent number
US05614498

Reaction notes

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