2,6-Lutidine → HCID 15460467, compound

HRID 2187352Notes

Reaction equation

HRID 2187352 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C@H:8]1[C@H:33]([OH:34])[C@@:32]2([CH3:35])[C:11](=[CH:12][CH:13]=[C:14]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:27])[CH2:20][CH2:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[CH2:10][C@H:9]1[OH:37])(=[O:3])[CH3:2].N1C(C)=CC=C[C:39]=1[CH3:45].FC(F)(F)S(O[Si:52]([CH2:57][CH3:58])([CH2:55][CH3:56])[CH2:53][CH3:54])(=O)=O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][O:7][C@H:8]1[C@H:33]([O:34][Si:52]([CH2:57][CH3:58])([CH2:55][CH3:56])[CH2:53][CH3:54])[C@@:32]2([CH3:35])[C:11](=[CH:12][CH:13]=[C:14]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:27])[CH2:20][CH2:21][CH2:22][C:23]([O:26][Si:52]([CH2:57][CH3:58])([CH2:55][CH3:56])[CH2:53][CH3:54])([CH3:25])[CH3:24])[CH2:10][C@H:9]1[O:37][Si:52]([CH2:39][CH3:45])([CH2:55][CH3:56])[CH2:53][CH3:54])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 15460466HCID 15460466, compound

Product 1

HCID 15460467HCID 15460467, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (15 ml) solution of compound 3 (260 mg, 502 μmol) obtained in Example 1, and 2,6-lutidine (877 μl, 7.53 mmol), triethylsilyl trifluoromethanesulfonate (1.14 ml, 5.02 mmol) was added with ice cooling in an argon atmosphere, and the mixture was stirred for 1.5 hours at the same temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (5% ethyl acetate/hexane) to give colorless oily compound 4 (327 mg, 76%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by flash column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-730d6fb34c174488b5deb5bda05369ac
Source dataset
uspto-grants-2002_06
Patent number
US06410523B1

Reaction notes

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