Triethylamine → (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl methanesulfonate

HRID 451856Notes

Reaction equation

HRID 451856 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1.C(N(CC)CC)C.[S:26](Cl)([CH3:29])(=[O:28])=[O:27]>C(Cl)Cl>[CH3:29][S:26]([O:1][CH2:2][C@@H:3]([NH:11][C:12]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:18])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58011540tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

Product 1

HCID 58017432(S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl methanesulfonateYield 111.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (6.2 g, 23.9 mmol) and triethylamine (7.25 g, 71.8 mmol) in CH2Cl2 at 0° C. was added mesyl chloride (5.5 g, 47.8 mmol) dropwise. The reaction mixture was stirred at rt until the starting material disappeared. The reaction was quenched with ice-cold water and extracted with CH2Cl2 (3×100 ml). The combined organic layers were washed with water (3×50 ml), dried over Na2SO4, and concentrated under vacuo to give the (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl methanesulfonate (9 g), which was used for the next step without purification.

Workup

  1. customThe reaction was quenched with ice-cold water
  2. extractionextracted with CH2Cl2 (3×100 ml)
  3. washThe combined organic layers were washed with water (3×50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-ca0308e141124eecb233e56c1b54b7c9
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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