2-Dimethylaminopyridine → HCID 56614900, compound

HRID 2288072Notes

Reaction equation

HRID 2288072 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:47]([OH:48])[CH:41]6[CH:42]([O:43][C:44](=[O:46])[CH3:45])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:49]([CH3:51])[CH3:50])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.FC(F)(F)S(O[Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])(=O)=O>ClCCl>[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:47]([O:48][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[CH:41]6[CH:42]([O:43][C:44](=[O:46])[CH3:45])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:49]([CH3:51])[CH3:50])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 56621158HCID 56621158, compound

Product 1

HCID 56614900HCID 56614900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg of compound (3) was dissolved in 0.7 ml of anhydrous dichloromethane and stirred together with 70 mg of dimethylaminopyridine and 49 μl of t-butyldimethylsilyl trifluoromethanesulfonate for 1 hour under cooling with ice. The reaction solution was concentrated in vacuo, dissolved in methanol, charged onto a silica gel column (Kieselgel 60, Merck, 1.5φ×22 cm) and eluted with n-hexane-ethyl acetate (4:1). The fraction containing the desired product was concentrated in vacuo to give 99 mg of compound (5) as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction solution was concentrated in vacuo
  3. dissolutiondissolved in methanol
  4. additioncharged onto a silica gel column (Kieselgel 60, Merck, 1.5φ×22 cm)
  5. washeluted with n-hexane-ethyl acetate (4:1)
  6. additionThe fraction containing the desired product
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-3ba1ae78a8934a60914f8408ed188c72
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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