Tetrabutylammonium Fluoride → HCID 178505099, compound

HRID 705351Notes

Reaction equation

HRID 705351 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([S:37]([CH3:40])(=[O:39])=[O:38])[C:14]1[C:33]([CH:34]2[CH2:36][CH2:35]2)=[CH:32][C:17]2[C:18]([C:28](=[NH:31])[NH:29][OH:30])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[O:20][C:16]=2[CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:34]1([C:33]2[C:14]([N:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[S:37]([CH3:40])(=[O:38])=[O:39])=[CH:15][C:16]3[O:20][C:19]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[C:18]([C:28](=[NH:31])[NH:29][OH:30])[C:17]=3[CH:32]=2)[CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455217HCID 178455217, compound

Product 1

HCID 178505099HCID 178505099, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 11C (0.1193 g, 0.202 mmol) in tetrahydrofuran (5 mL) was treated with 1 M tetrabutylammonium fluoride in tetrahydrofuran (0.607 mL, 0.607 mmol), and the resulting yellow solution was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated in vacuo, the yellow oily residue was taken up in dichloromethane (10 mL), filtered, and purified on a silica gel column (12 g) eluting with a gradient of 99.5/0.5 dichloromethane/methanol to 95/5 dichloromethane/methanol over 30 minutes to afford the title compound (0.095 g, 99%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered
  3. custompurified on a silica gel column (12 g)
  4. washeluting with a gradient of 99.5/0.5 dichloromethane/methanol to 95/5 dichloromethane/methanol over 30 minutes

Sources & evidence

ORD record
ord-7efda773cccf463386a119b162890c67
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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