2,6-Lutidine → HCID 87901166, compound

HRID 1796861Notes

Reaction equation

HRID 1796861 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7].FC(F)(F)S(O[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])(=O)=O.N1C(C)=CC=CC=1C>ClCCl>[Si:23]([O:1][CH2:2][CH2:3][CH2:4][C@H:5]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 87901161HCID 87901161, compound

Product 1

HCID 87901166HCID 87901166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 8F (2.58 g, 11.1 mmol), tert-butyldimethylsilyl trifluoromethanesulfonate (2.8 mL, 12 mmol), and 2,6-lutidine (1.5 mL, 13 mmol) in dichloromethane (100 mL) at 0° C. was stirred for 2 hours, diluted with dichloromethane, washed sequentially with 10% KHSO4, aqueous NaHCO3, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 346 (M+H)+.

Workup

  1. washwashed sequentially with 10% KHSO4, aqueous NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e06f87f8868c41fa96fbd0142adc650b
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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